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

Patent metadata

Field	Value
Publication number	US-10193080-B2
Application number	US-201514804898-A
Country	US
Kind code	B2
Filing date	Jul 21, 2015
Priority date	Oct 23, 2014
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

A condensed cyclic compound represented by Formulae 1A or 1B:

wherein in Formulae 1A and 1B, groups and variables are the same as described in the specification.

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formulae 1A or 1B:

wherein in Formulae 1A and 1B,
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, C or C(R 15 ), X 16 is N, C or C(R 16 ), X 17 is N, C, or C(R 17 ), and X 18 is N, C, or C(R 18 ), and when X 15 is C, X 15 is connected with *-(L 2 ) a2 -*′, when X 16 is C, X 16 is connected with *-(L 2 ) a2 -*′, when X 17 is C, X 17 is connected with *-(L 2 ) a2 -*′, and when X 18 is C, X 18 is connected with *-(L 2 ) a2 -*′,
X 21 is selected from O, S, Se, C(R 21 )(R 22 ), Si(R 21 )(R 22 ), and N(R 23 ),
X 22 is selected from O, S, Se, C(R 24 )(R 25 ), Si(R 24 )(R 25 ), and N(R 26 ),
X 23 is selected from O, S, Se, C(R 27 )(R 28 ), and Si(R 27 )(R 28 ),
L 1 and L 2 are each independently selected from
a phenylene group, a pyridinylene group, a fluorenylene group, a dibenzofuranylene group, and a dibenzothiophenylene group;
a phenylene group, a pyridinylene group, a fluorenylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, each substituted with at least one of 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 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(R 41 )(R 42 )—, —O—, —S—, and —Se—,
wherein a1 and a2 are each independently an integer selected from 0 to 5, and when a1 is 2 or more, 2 or more groups L 1 are identical to or different from each other, and when a2 is 2 or more, 2 or more groups L 2 are identical to or different from each other,
provided that when a1 is 1, L 1 is selected from
a phenylene group, a fluorenylene group, a dibenzofuranylene group, and a dibenzothiophenylene group;
a phenylene group, a fluorenylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, each substituted with at least one of 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 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 );
R 1 to R 8 , R 11 to R 18 , and R 31 to R 34 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 of 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 of 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, 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 11 )(Q 12 )(Q 13 ); and
—Si(Q 21 )(Q 22 )(Q 23 ), and
b1 and b3 are each independently 1, 2, or 3, and b2 and b4 are each independently 1, 2, 3, or 4, and when b1 is 2 or more, 2 or more groups R 31 are identical to or different from each other, when b2 is 2 or more, 2 or more groups R 32 are identical to or different from each other, when b3 is 2 or more, 2 or more groups R 33 are identical to or different from each other, and when b4 is 2 or more, 2 or more groups R 34 are identical to or different from each other,
in Formula 1A, i) at least one of X 3 and X 7 is C(CN), ii) at least one of groups R 31 (s) in the number of b1 and groups R 32 in the number of b2 is a cyano group, or iii) at least one of X 3 and X 7 is C(CN) and at least one of groups R 31 in the number of b1 and groups R 32 in the number of b2 is a cyano group,
in Formula 1B, i) at least one of X 13 and X 17 is C(CN), ii) at least one of groups R 33 in the number of b3 and groups R 34 in the number of b4 is a cyano group, or iii)) at least one X 13 and X 17 is C(CN) and at least one of groups R 33 in the number of b3 and groups R 34 in the number of b4 is a cyano group,
R 21 to R 29 , R 41 , R 42 , Q 1 to Q 3 , Q 11 to Q 13 , and Q 21 to Q 23 are each independently selected from
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 of 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; and
a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one of 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, a C 1 -C 20 alkoxy group, a phenyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

2. The condensed cyclic compound of claim 1 , wherein in Formulae 1A, X 1 is C(R 1 ), X 2 is C(R 2 ), X 3 is C(R 3 ), X 4 is C(R 4 ), X 5 is C(R 5 ), X 6 is C(R 6 ), X 7 is C(R 7 ), X 8 is C(R 8 ), X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), and X 14 is C(R 14 ).

3. The condensed cyclic compound of claim 1 , wherein R 1 , R 2 , R 4 , R 5 , R 6 , and R 8 in Formula 1A are not a cyano group, and R 11 , R 12 , and R 14 in Formula 1B are not a cyano group.

4. The condensed cyclic compound of claim 1 , wherein in Formula 1B,
X 21 is selected from O, S, C(R 21 )(R 22 ), and N(R 23 ),
X 22 is selected from O, S, C(R 24 )(R 25 ), and N(R 26 ),
X 23 is selected from O, S, and C(R 27 )(R 28 ),
R 21 , R 22 , R 24 , R 25 , R 27 , and R 28 are each independently selected from
a C 1 -C 20 alkyl group and a C 1

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

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

Classifications

• C07D209/88 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• H01L51/5012

  Electricity · mapped topic

• H01L51/0073

  Electricity · mapped topic