Condensed cyclic compound and organic light-emitting diode comprising the same

Patent metadata

Field	Value
Publication number	US-9520566-B2
Application number	US-201314012073-A
Country	US
Kind code	B2
Filing date	Aug 28, 2013
Priority date	Jan 16, 2013
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

A condensed cyclic compound represented by Formula 1 below and an organic light-emitting device (OLED) including the condensed cyclic compound are presented.

Ar 1 and Ar 2 in Formula 1 are each independently one of a hydrogen atom, an aryl or heteroaryl group and an arylamino group, at least one of Ar 1 and Ar 2 being a substituted or unsubstituted 1,2,4-triazol-4-yl group; L 1 and L 2 in Formula 1 are linking groups, each independently one of a cyclic or noncyclic, saturated or unsaturated hydrocarbon group and a heteroarylene group; a and b in Formula 1 are each independently one of 0 or 1; and R 1 to R 8 in Formula 1 being each independently one of a variety of inorganic and organic substituents including cyclic or noncyclic, saturated or unsaturated and aromatic, nonaromatic or heteraromatic groups. The OLED may have a low driving voltage, a high emission efficiency and long lifespan characteristics.

First claim

What is claimed is:

1. A condensed cyclic compound of Formula 1 below:

Formula 1Ar 1 and Ar 2 in Formula 1 being each independently one of a hydrogen atom, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, and a substituted or unsubstituted C 1 -C 60 arylamino group, at least one of Ar 1 and Ar 2 being a substituent represented by Formula 2F below:

Formula 2F, Z 11 being one of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a fluorenyl group, and a quinolyl group, a plurality of Z 11 s being identical to or different from each other;
p being an integer selected from 1 to 4;
indicating a binding site;
L 1 and L 2 in Formula 1 being each independently one of a substituted or unsubstituted C 1 -C 60 alkylene group, a substituted or unsubstituted C 3 -C 60 cycloalkylene group, a substituted or unsubstituted C 2 -C 60 alkenylene group, a substituted or unsubstituted C 5 -C 60 cycloalkenylene group, a substituted or unsubstituted C 2 -C 60 alkynylene group, a substituted or unsubstituted C 5 -C 60 cycloalkynylene group, a substituted or unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted C 5 -C 60 heteroarylene group;
a and b in Formula 1 being each independently 0 or 1; and
R 1 to R 8 in Formula 1 being each independently one of a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl 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 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 3 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, —N(Q 1 )(Q 2 ) and —Si(Q 3 )(Q 4 )(Q 5 ) (where Q 1 to Q 5 are each independently one of a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, and a C 2 -C 60 heteroaryl group).

2. The condensed cyclic compound of claim 1 , Ar 1 and Ar 2 being each independently one of a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pentaphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted indacenyl group, a substituted or unsubstituted acenaphthyl group, a substituted or unsubstituted heptalenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted hexacenyl group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted a pyridyl group, a substituted or unsubstituted a pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolizinyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted isobenzofuryl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzisoxazolyl group, a substituted or unsubstituted imidazopyridyl group, a substituted or unsubstituted purinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridoindolyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted benzoquinolyl group, a substituted or unsubstituted phenazinyl group, and a substituted or unsubstituted dibenzothiophenyl group.

3. The condensed cyclic compound of claim 1 , Ar 1 and Ar 2 being each independently one of a hydrogen atom and a substituent represented by one of Formulae 2A to 2G below:

Z 11 being one of a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a phenyl group, a naphthyl group, an anthryl group, a pyridyl group, a fluorenyl group, and a quinolyl group, a plurality of Z 11 s being identical to or different from each other;
p being an integer selected from 1 to 7; and
* indicates a binding site.

4. The condensed cyclic compound of claim 1 , Ar 1 and Ar 2 being each independently a group represented by one of Formulae 3A to 3J, at least one of Ar 1 and Ar 2 being a group represented by Formula 3J:

5. The condensed cyclic compound of claim 1 , L 1 and L 2 being each independently one of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstitut

Assignees

• Samsung Display Co Ltd
• Duksan High Metal Co Ltd
• Duk San Neolux Co Ltd

Inventors

• Kim Seul-Ong
• Kwon O-Hyun
• Shin Dong-Woo
• Park Mie-Hwa
• Lee Bum-Sung

Classifications

• H01L51/0058

  Electricity · mapped topic

• C09K2211/1416

  Condensed systems · CPC title

• H01L51/0067

  Electricity · mapped topic

• H01L51/0054 Primary

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic