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

Patent metadata

Field	Value
Publication number	US-10367151-B2
Application number	US-201615012266-A
Country	US
Kind code	B2
Filing date	Feb 1, 2016
Priority date	Jun 23, 2015
Publication date	Jul 30, 2019
Grant date	Jul 30, 2019

Abstract

A condensed cyclic compound represented by Formula 1:

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

First claim

What is claimed is:

1. A condensed cyclic compound represented by one of Formulae 1A to 1D:

L 1 to L 3 are each independently selected from the group consisting of
a phenylene group, a fluorenylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and
a substituted or unsubstituted phenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, and substituted or unsubstituted a dibenzothiophenylene group, wherein each substituted group is 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 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,
a1 to a3 are each independently an integer selected from 0 to 5, wherein when a1 is 2 or greater, two or more groups L 1 are identical to or different from each other, when a2 is 2 or greater, two or more groups L 2 are identical to or different from each other, and when a3 is 2 or greater, two or more groups L 3 are identical to or different from each other,
R 1 to R 7 , and R 11 to R 18 are each independently selected from the group consisting of:
a hydrogen, a deuterium, —F, a cyano group, 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, and a cyano group;
a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and
a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,
a group represented by

is selected from groups consisting of groups represented by Formulae 5-1 to 5-60, and a group represented by

is selected from groups consisting of groups represented by Formulae 5-1 to 5-69:

wherein, in Formulae 5-1 to 5-69, * is a binding site to a neighboring atom.

2. The condensed cyclic compound of claim 1 , wherein L 1 to L 3 are each independently selected from groups consisting of groups represented by Formulae 3-1, 3-15, 3-28, and 3-41 to 3-56:

wherein, in Formulae 3-1, 3-15, 3-28, and 3-41 to 3-56,
Y 1 is selected from the group consisting of O, S, and C(Z 3 )(Z 4 ),
Z 1 to Z 4 are each independently selected from the group consisting of 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 C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,
d4 is an integer selected from 0 to 4,
d3 is an integer selected from 0 to 3,
and
* and *′ are each a binding site to a neighboring atom.

3. The condensed cyclic compound of claim 2 , wherein
i) a1 is 0; or
ii) when a1 is not 0, at least one of groups Li is selected from groups consisting of groups represented by Formulae 3-15, 3-28, and 3-41 to 3-56.

4. The condensed cyclic compound of claim 2 , wherein
L 1 is selected from groups consisting of groups represented by Formulae 3-15, 3-28, 3-41, and 3-51,
L 2 and L 3 are each independently selected from groups consisting of groups represented by Formulae 3-1, 3-15, 3-28, 3-41, and 3-51, and
a1 to a3 are each independently 0, 1, or 2.

5. The condensed cyclic compound of claim 1 , wherein a group represented by *-(L 1 ) a1 -*′ is selected from groups consisting of groups represented by Formulae 4-1 to 4-39:

wherein, in Formulae 4-1 to 4-39,
X 21 is C(Z 21 ), X 22 is C(Z 22 ), X 23 is C(Z 23 ), X 24 is C(Z 24 ), X 31 is C(Z 31 ), X 32 is C(Z 32 ), X 33 is C(Z 33 ), X 34 is C(Z 34 ), X 41 is C(Z 41 ), X 42 is C(Z 42 ), X 43 is C(Z 43 ), and X 44 is C(Z 44 ),
Z 21 to Z 24 , Z 31 to Z 34 , and Z 41 to Z 44 are each independently selected from the group consisting of a hydrogen, a deuterium, a cyano group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group,
* and * 1 are each a binding site to a neighboring atom.

6. The condensed cyclic compound of claim 1 , wherein at least one of R 3 , R 6 , R 13 , and R 16 is CN.

7. A condensed cyclic compound, being one of Compounds 1 to 271:

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

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

Classifications

• C07D409/14

  containing three or more hetero rings · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• B32B2457/206

  Organic displays, e.g. OLED · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title