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

Patent metadata

Field	Value
Publication number	US-9653689-B2
Application number	US-201514969767-A
Country	US
Kind code	B2
Filing date	Dec 15, 2015
Priority date	Jan 17, 2011
Publication date	May 16, 2017
Grant date	May 16, 2017

Abstract

A condensed-cyclic compound represented by Formula 1 below, and an organic light-emitting diode including the condensed-cyclic compound.

wherein R 1 through R 6 , Ar 5 and Ar 6 , and X 1 through X 10 are defined as in the specification.

First claim

What is claimed is:

1. A condensed-cyclic compound represented by Formula 1A below:

wherein R 1 is represented by —(Ar 1 ) a1 —(R 11 ) b1 , R 2 is represented by —(Ar 2 ) a2 —(R 12 ) b2 , R 3 is represented by —(Ar 3 ) a3 —(R 13 ) b3 , and R 4 is represented by —(Ar 4 ) a4 —(R 14 ) b4 ;
Ar 1 through Ar 4 are each independently a substituted or unsubstituted C 6 -C 60 aromatic linking group or a substituted or unsubstituted C 2 -C 60 heteroaromatic linking group;
Ar 5 and Ar 6 are each independently a substituted or unsubstituted C 6 -C 60 arylene group or a substituted or unsubstituted C 2 -C 60 heteroarylene group;
R 11 through R 14 are each independently non-covalent electron pairs, hydrogen, deuterium, 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 60 cycloalkyl 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, or a substituted or unsubstituted C 2 -C 60 condensed-cyclic group;
a1 through a4 are each independently an integer of 0 to 3;
b1 through b4 are each independently an integer of 1 to 5;
c and d are each independently an integer of 0 to 3;
X 1 through X 10 are each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid 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 60 cycloalkyl 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, —Si(R 21 )(R 22 )(R 23 ), or —N(R 24 )(R 25 );
R 21 through R 25 are each independently hydrogen, deuterium, 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 60 cycloalkyl 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, or a substituted or unsubstituted C 2 -C 60 heteroaryl group;
Z 21 and Z 22 are each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid 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, or a substituted or unsubstituted C 1 -C 60 alkoxy group;
u is an integer of 1 to 4; and
v is an integer of 1 to 6.

2. The condensed-cyclic compound of claim 1 , wherein R 11 through R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted heptalenyl group, a substituted or unsubstituted indacenyl group, a substituted or unsubstituted acenaphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pentaphenyl group, a substituted or unsubstituted hexacenyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cycloheptyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted tetrahydronaphthyl group, or a substituted or unsubstituted dihydro-indenyl group.

3. The condensed-cyclic compound of claim 1 , wherein Ar 1 through Ar 4 are each independently a substituted or unsubstituted benzene linking group, a substituted or unsubstituted pentalene linking group, a substituted or unsubstituted indene linking group, a substituted or unsubstituted naphthalene linking group, a substituted or unsubstituted azulene linking group, a substituted or unsubstituted heptalene linking group, a substituted or unsubstituted indacene linking group, a substituted or unsubstituted acenaphthylene linking group, a substituted or unsubstituted fluorene linking group, a substituted or unsubstituted phenalene linking group, a substituted or unsubstituted phenanthrene linking group, a substituted or unsubstituted anthracene linking group, a substituted or unsubstituted fluoranthene linking group, a substituted or unsubstituted triphenylene linking group, a substituted or unsubstituted pyrene linking group, a substituted or unsubstituted crycene linking group, a substituted or unsubstituted naphthacene linking group, a substituted or unsubstituted pycene linking group, a substituted or unsubstituted perylene linking group, a substituted or unsubstituted pentacene linking group, or a substituted or unsubstituted hexacene linking group.

4. The condensed-cyclic compound of claim 1 , wherein a 1 through a 4 are each independently 0, 1, or 2, and b 1 through b 4 are each independently 1 or 2.

5. The condensed-cyclic compound of claim 1 , wherein R 11 through R 14 are each independently one of hydrogen; deuterium; a C 1 -C 10 alkyl group; a phenyl group; a naphthyl group; a phenanthrenyl group; a fluorenyl group; a pyrenyl group; a cyclopentyl group; a cyclohexyl group; a tetrahydronaphthyl group; a dihydro-indenyl group; and a phenyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, a pyrenyl group, a cyclopentyl group, a cyclohexyl group, a tetrahydronaphthyl group, and a dihydro-indenyl group that are substituted with at least one of deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, and —Si(Q 1 )(Q 2 )(Q 3 );
Q 1 through Q 3 are each independently a C 1 -C 10 alkyl group or a C 6 -C 14 aryl group;
Ar 1 through Ar 4 are each independently represented by one of Formulae 3A through 3G below:

Assignees

• Samsung Display Co Ltd
• Sfc Co Ltd

Inventors

• Kim Myeong-Suk
• Je Jong-Tae
• Lee Se-Jin
• Park Seok-Bae
• Yu Se-Jin
• Lim Jea-Geon
• Choi Byoung-Ki
• Kim Tae-Kyung
• Yi Jeoung-In

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• H01L51/0052

  Electricity · mapped topic

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07F7/0818

  Chemistry & Metallurgy · mapped topic

• H01L51/0067

  Electricity · mapped topic