Carbazole-based compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10505124-B2
Application number	US-201514669102-A
Country	US
Kind code	B2
Filing date	Mar 26, 2015
Priority date	Oct 31, 2014
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

A carbazole compound represented by Formula 1:

wherein in Formula 1, groups X 1 to X 8 , X 11 to X 19 , and R 41 to R 43 are the same as in the specification.

First claim

What is claimed is:

1. A carbazole compound represented by Formula 1:

wherein in the Formulae 1, 2A(2), 2B, 2C, and 2D,
X 1 is N or C(R 1 ), X 2 is N or C(R 2 ), X 3 is N or C(R 3 ), X 4 is N or C(R 4 ), X 5 is N or C(R 5 ), X 6 is N or C(R 6 ), X 7 is N or C(R 7 ), X 8 is N or C(R 8 ), X 11 is N or C(R 11 ), X 12 is N or C(R 12 ), X 13 is N or C(R 13 ), X 14 is N or C(R 14 ), X 15 is N or C(R 5 ), X 16 is N or C(R 16 ), X 17 is N or C(R 7 ), X 18 is N or C(R 8 ), X 19 is C(R 19 ) wherein R 19 is a hydrogen, X 22 is N, C or C(R 22 ), X 23 is N, C or C(R 23 ), X 24 is N, C or C(R 24 ), X 25 is N, C or C(R 25 ), X 26 is N, C or C(R 26 ), X 31 is N, C or C(R 31 ), X 32 is N, C or C(R 32 ), X 33 is N, C or C(R 33 ), X 34 is N, C or C(R 34 ), and X 35 is N, C or C(R 35 ),
provided that at least one selected from X 1 to X 8 and X 11 to X 18 is N,
provided that when X 22 is C, X 22 is connected to a carbon of a phenyl group of Formula 2B, when X 23 is C, X 23 is connected to a carbon of a phenyl group of Formula 2B, when X 24 is C, X 24 is connected to a carbon of a phenyl group of Formula 2B, when X 25 is C, X 25 is connected to a carbon of a phenyl group of Formula 2B, when X 26 is C, X 26 is connected to a carbon of a phenyl group of Formula 2B, when X 31 is C, X 31 is connected to a carbon of a phenyl group of Formulae 2C and 2D, when X 32 is C, X 32 is connected to a carbon of a phenyl group of Formulae 2C and 2D, when X 33 is C, X 33 is connected to a carbon of a phenyl group of Formulae 2C and 2D, when X 34 is C, X 34 is connected to a carbon of a phenyl group of Formulae 2C and 2D, when X 35 is C, X 35 is connected to a carbon of a phenyl group of Formulae 2C and 2D, one selected from X 22 to X 26 in Formula 2B is C, and one selected from X 31 to X 35 in Formulae 2C and 2D is C,
R 1 to R 8 , R 11 to R 18 , R 21 to R 27 , and R 31 to R 38 are each independently selected from
a hydrogen, a deuterium, —F, 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 20 alkyl group, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from a deuterium, —F, 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 and a phosphoric acid group or a salt thereof;
a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a hydroxyl 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 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 1 )(Q 2 )(Q 3 ); and
—Si(Q 11 )(Q 12 )(Q 13 ),
a1, a3, and a5 are each independently an integer selected from 1 to 4, and a2, a4 and a6 are each independently an integer selected from 1 to 5,
each of R 22 to R 26 is not a cyano group,
at least one of groups R 27 in the number of a2 in Formula 2B is a cyano group, at least one selected from R 31 to R 35 , groups R 36 in the number of a3 and groups R 37 in the number of a4 in Formula 2C is a cyano group, and at least one selected from R 31 to R 35 , groups R 36 in the number of a3, groups R 37 in the number of a5, and groups R 38 in the number of a6 in Formula 2D is a cyano group,
R 41 to R 43 are each independently selected from
groups represented by Formulae 2A(2), 2B, 2C, and 2D;
a hydrogen, a deuterium, —F, 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 20 alkyl group, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one selected from a deuterium, —F, 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 and a phosphoric acid group or a salt thereof;
a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a hydroxyl 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 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 21 )(Q 22 )(Q 23 ); and
—Si(Q 31 )(Q 32 )(Q 33 ),
at least one selected from R 41 to R 43 is a group represented by one of Formulae 2A(2), 2B, 2C, and 2D, and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently selected from a hydrogen, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

2. The carbazole compound of claim 1 , wherein
R 1 to R 8 , R 11 to R 18 , R 21 to R 27 , and R 31 to R 38 are each independently selected from
a hydrogen, a deuterium, —F, 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 10 alkyl group, and a C 1 -C 10 alkoxy group;
a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group, each substituted with at least one selected from a deuterium, —F, 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 and a phosphoric acid group or a salt thereof;
a phenyl group and a pyridinyl group;
a phenyl group and a pyridinyl group, each substituted with at least one selected from a deuterium, —F, a hydroxyl 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 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, and —Si(Q 1 )(Q 2 )(Q 3 ); and
—Si(Q 11 )(Q 12 )(Q 13 ),
a1 to a6 are each independently an integer selected from 1 to 3,
Q 1 to Q 3 and Q 11 to Q 13 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group and a pyridinyl group,
R 22 to R 26 are not a cyano group, and
at least one

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Kim Hyunjung
• Chae Miyoung
• Huh Dalho
• Kim Sangmo
• Son Jhunmo
• Jeon Soonok
• Chung Yeonsook
• Jung Yongsik
• Lee Namheon

Classifications

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D401/14 Primary

  containing three or more hetero rings · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title