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

Patent metadata

Field	Value
Publication number	US-10062853-B2
Application number	US-201615346090-A
Country	US
Kind code	B2
Filing date	Nov 8, 2016
Priority date	Jun 9, 2016
Publication date	Aug 28, 2018
Grant date	Aug 28, 2018

Abstract

A condensed cyclic compound represented by Formula 1:

Ar 1 -L 1 -L 2 -Ar 2   Formula 1
wherein in Formula 1, Ar 1 , Ar 2 , L 1 , and L 2 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,
Ar 1 is a group represented by Formula 2,
Ar 2 is a group represented by Formula 3,
L 1 is selected from a group represented by Formula 4A, a group represented by Formula 4B, and a group represented by Formula 4C, L 2 is selected from a group represented by Formula 4D, a group represented by Formula 4E, and a group represented by Formula 4F, wherein a case in which L 1 is the group represented by Formula 4C and L 2 is the group represented by Formula 4F is excluded,
R 1 to R 4 , R 11 to R 14 , R 21 to R 24 , R 31 to R 34 , and R 41 to R 49 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group (CN), 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 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group (provided that the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group is not a substituted or unsubstituted carbazolyl group), —N(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ),
the number of cyano group(s) (CN) in a group represented by *-L 1 -L 2 -*′ in Formula 1 is 1, 2, 3, or 4,
a1 to a9 are each independently an integer selected from 0 to 5,
* and *′ each indicate a binding site to a neighboring atom,
at least one of substituents of the substituted carbazolyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 1 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from
deuterium, —CD 3 , —CD 2 H, —CDH 2 , 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 C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group (provided that the non-aromatic condensed heteropolycyclic group is not a carbazolyl group);
a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group (provided that the non-aromatic condensed heteropolycyclic group is not a carbazolyl group), each substituted with at least one selected from deuterium,—CD 3 , —CD 2 H, —CDH 2 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazine 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, C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group (provided that the non-aromatic condensed heteropolycyclic group is not a carbazolyl group), —N(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ); and
—N(Q 34 )(Q 35 ) and —B(Q 36 )(Q 37 ),
wherein Q 4 to Q 7 , Q 24 to Q 27 and Q 34 to Q 37 are each independently selected from hydrogen, deuterium, 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 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 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group (provided that the substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group is not a substituted or unsubstituted carbazolyl group).

2. The condensed cyclic compound of claim 1 , wherein
R 1 to R 4 , R 11 to R 14 , R 21 to R 24 , R 31 to R 34 , and R 41 to R 49 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group (CN), 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 biphenyl group, a terphenyl 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-bifluorenyl 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 benzooxazolyl group, a benzimidazolyl 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, imidazopyrimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzooxazinyl group, and a pyridobenzothiazinyl group;
a phenyl group, a biphenyl group, a terphenyl 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 p

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Jung Yongsik
• Chae Miyoung
• Son Jhunmo
• Huh Dalho
• Kwon Eunsuk
• Kim Sangmo
• LEE Saeyoun
• Jeon Soonok
• Chung Yeonsook
• Kang Hosuk
• Kim Jongsoo

Classifications

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• H01L51/5096

  Electricity · mapped topic

• C07D209/86 Primary

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

• H01L51/0072 Primary

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic