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

Patent metadata

Field	Value
Publication number	US-10043984-B2
Application number	US-201514969257-A
Country	US
Kind code	B2
Filing date	Dec 15, 2015
Priority date	Jul 1, 2015
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

A condensed cyclic compound represented by Formula 1, comprising at least one cyano (—CN) group:

wherein, in Formula 1, groups and variables 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,
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 15 ), X 16 is N or C(R 16 ), X 17 is N or C(R 17 ), and X 18 is N or C(R 18 ),
Y 11 is O, S, C(R 101 )(R 102 ), or Si(R 101 )(R 102 ),
R 1 to R 8 are independently selected from
a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, and a triazinyl group;
a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group;
a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, and —Si(Q 31 )(Q 32 )(Q 33 ); and
—Si(Q 1 )(Q 2 )(Q 3 ),
R 11 to R 18 , R 101 , and R 102 each are independently selected from:
a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano (—CN) 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 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl 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 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 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 1 )(Q 2 )(Q 3 ), wherein the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group does not comprise a substituted or an unsubstituted carbazolyl group, and R 101 and R 102 are optionally linked to each other to form a saturated or unsaturated ring,
Ar is a group represented by one of Formulae 2A to 2D:

wherein, in Formulae 2A to 2D,
* and *′ each independently indicate a binding site to a neighboring atom,
X 21 is N or C(R 21 ), X 22 is N or C(R 22 ), X 23 is N or C(R 23 ), and X 24 is N or C(R 24 ), Y 21 is O, S, P(═O) 2 , Se, C(R 25 )(R 26 ), or Si(R 25 )(R 26 ),
R 21 to R 26 each are independently selected from a hydrogen, a deuterium, a C 1 -C 4 alkyl group, a C 6 -C 20 aryl group, a C 1 -C 20 heteroaryl group, and —Si(Q 11 )(Q 12 )(Q 13 ),
b21 and b22 each are independently selected from integers of 1 to 3, provided that when b21 is 2 or more, groups R 21 are identical to or different from each other, and provided that when b22 is 2 or more, groups R 22 are identical to or different from each other,
L 11 and L 12 each are independently selected from:
a phenylene grou

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Jeon Soonok
• Kim Sangmo
• Kim Hyungjun
• Chung Yeonsook
• Jung Yongsik
• Chae Miyoung
• Huh Dalho
• Kim Joonghyuk
• Ihn Sooghang

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1022

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C07D401/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title