Compound and organic light-emitting device comprising same

Patent metadata

Field	Value
Publication number	US-9065060-B2
Application number	US-201213979956-A
Country	US
Kind code	B2
Filing date	Jan 17, 2012
Priority date	Jan 17, 2011
Publication date	Jun 23, 2015
Grant date	Jun 23, 2015

Abstract

The present invention relates to a novel compound and an organic light emitting device comprising the same. The compound according to the present invention may be used as hole injection, hole transport, electron injection and transport, and light emitting materials in an organic light emitting device, and the organic light emitting device according to the present invention has excellent properties in terms of efficiency, driving voltage, and life-span.

First claim

The invention claimed is:

1. A compound represented by the following Chemical Formula 1:

wherein,
Ar 1 is hydrogen;
Ar 2 and Ar 3 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; an alkyl group unsubstituted or substituted by one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, a heterocyclic group, a nitrile group, and an acetylene group; an alkoxy group unsubstituted or substituted by one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, a heterocyclic group, a nitrile group, and an acetylene group; an aryl group unsubstituted or substituted by one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, a heterocyclic group, a nitrile group, an acetylene group, and an arylamine group; a heterocyclic group unsubstituted or substituted by one or more substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, a heterocyclic group, a nitrile group, and an acetylene group; and an amine group unsubstituted or substituted by one or more substituent groups selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group,
at least one of Ar 2 and Ar 3 is an amine group unsubstituted or substituted by a phenyl group, a biphenyl group, a terphenyl group, stilben, a naphthyl group, an anthracenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a heterocyclic group, or a fluorenyl group; or an aryl group substituted by an amine group unsubstituted or substituted by an aryl group, a heterocyclic group, or a fluorenyl group, and may be further substituted by an aryl group, a fluorene group, or an amine group substituted by a substituent selected from the group consisting of an aryl group and a heterocyclic group,
R 1 and R 2 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; and a heterocyclic group,
R 3 is selected from the group consisting of hydrogen; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; and a heterocyclic group, and
p is an integer of 1 to 5, q is an integer of 1 or 2, and r is an integer of 1 to 4.

2. The compound of claim 1 , wherein Chemical Formula 1 is represented by the following Chemical Formulas 2 to 5:

wherein,
Ar 4 , Ar 7 , Ar 10 , and Ar 14 are hydrogen,
Ar 5 , Ar 6 , Ar 8 , Ar 9 , Ar 11 , Ar 12 , Ar 13 , Ar 15 , Ar 16 , and Ar 17 are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted fluorenyl group,
L 1 , L 2 , L 3 and L 5 are a direct bond, an arylene group, or a fluorenylene group, and
L 4 and L 6 are an arylene group,
when L 1 is direct bond, Ar 5 and Ar 6 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilben, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted fluorenyl group,
when L 2 is direct bond, Ar 8 and Ar 9 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilben, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted fluorenyl group,
when L 3 is direct bond, Ar 11 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilben, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted fluorenyl group, and
when L 4 is direct bond, Ar 15 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted stilben, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted fluorenyl group.

3. The compound of claim 1 , wherein at least one of Ar 2 and Ar 3 of Chemical Formula 1 is an amine group unsubstituted or substituted by a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted by a fluorenyl group, a naphthyl group, a fluorenyl group substituted by an alkyl group, or a dibenzothiophenyl group.

4. The compound of claim 1 , wherein at least one of Ar 2 and Ar 3 of Chemical Formula 1 is a phenyl group substituted by an amine group unsubstituted or substituted by a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted by a fluorenyl group, a naphthyl group, a fluorenyl group substituted by an alkyl group, a dibenzothiophenyl group, or a phenanthrenyl group; a biphenyl group substituted by an amine group unsubstituted or substituted by a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted by a fluorenyl group, a naphthyl group, a fluorenyl group substituted by an alkyl group, a dibenzothiophenyl group, or a phenanthrenyl group; a fluorenyl group substituted by an amine group unsubstituted or substituted by a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted by a fluorenyl group, a naphthyl group, a fluorenyl group substituted by an alkyl group, a dibenzothiophenyl group, or a phenanthrenyl group; or a naphthyl group substituted by an amine group unsubstituted or substituted by a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted by a fluorenyl group, a naphthyl group, a fluorenyl group substituted by an alkyl group, a dibenzothiophenyl group, or a phenanthrenyl group.

5. The compound of claim 1 , wherein at least one of Ar 2 and Ar 3 of Chemical Formula 1 is the following substituent group

Assignees

• Hong Sung Kil
• Kim Yun Hwan
• Park Tae Yoon
• Jang Hye Young
• Jang Boonjae
• Lg Chemical Ltd

Inventors

• Hong Sung Kil
• Kim Yun Hwan
• Park Tae Yoon
• Jang Hye Young
• Jang Boonjae

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• H01L51/0074

  Electricity · mapped topic

• C09K2211/1014

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

• H01L51/0061

  Electricity · mapped topic

• H01L51/0052

  Electricity · mapped topic