Compound and organic light emitting device including the same

Patent metadata

Field	Value
Publication number	US-9246109-B2
Application number	US-201313800962-A
Country	US
Kind code	B2
Filing date	Mar 13, 2013
Priority date	Oct 19, 2012
Publication date	Jan 26, 2016
Grant date	Jan 26, 2016

Abstract

A compound represented by Formula 1, below, and an organic light-emitting device including the compound represented by Formula 1:

First claim

What is claimed is:

1. A compound represented by Formula 1 below:

wherein, in Formula 1,
R 1 is a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C3-C60 cycloalkenyl group, a substituted or unsubstituted C5-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted C5-C60 aryloxy group, a substituted or unsubstituted C5-C60 arylthio group; or a substituted or unsubstituted C6-C60 condensed polycyclic group,
Ar 1 to Ar 4 are each independently a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted C6-C60 condensed polycyclic group,
X and Y are each independently a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted C6-C60 condensed polycyclic group, or a divalent linking group formed by linking at least two of the arylene group, the heteroarylene group, and the condensed polycyclic groups.

2. The compound of claim 1 , wherein, in Formula 1:
Ar 1 , Ar 2 , or X are each independently linked to one another to form a ring, or
Ar 3 , Ar 4 , or Y are each independently linked to one another to form a ring.

3. The compound of claim 1 , wherein, in Formula 1, R 1 is a group represented by one of Formulae 2a-2d, below:

wherein, in Formulae 2a-2d,
Y 1 , Y 2 , and Y 3 are each independently C, or N;
Q 1 is a linking group represented by —C(R 30 )(R 31 )—, or —N(R 32 )—;
Z 1 , Z 2 , R 30 , R 31 , and R 32 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, —Si(R 40 ) 3 , a halogen group, a cyano group, a nitro group, a hydroxy group, or a carboxy group;
R 40 is a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, or a substituted or unsubstituted C6-C20 condensed polycyclic group;
p is an integer from 1 to 7; and
* indicates a binding site to a nitrogen atom.

4. The compound of claim 1 , wherein, in Formula 1, Ar 1 to Ar 4 are each independently a group represented by one of Formulae 3a to 3d, below:

wherein, in Formulae 3a to 3d,
Q 2 is a linking group represented by —C(R 30 )(R 31 )—, —N(R 32 )—, —S—, or —O—;
Z 1 , R 30 , R 31 , and R 32 are each independently, a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, —Si(R 40 ) 3 , a halogen group, a cyano group, a nitro group, a hydroxy group, or a carboxy group;
R 40 is a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, or a substituted or unsubstituted C6-C20 condensed polycyclic group;
p is an integer from 1 to 7; and
* indicates a binding site to a nitrogen atom.

5. The compound of claim 1 , wherein, in Formula 1, X and Y are each independently a group represented by one of Formulae 4a to 4f, below:

wherein, in Formulae 4a to 4f,
Q 3 is a linking group represented by —C(R 30 )(R 31 )—, —N(R 32 )—, or —O—;
R 30 , R 31 , and R 32 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 condensed polycyclic group, a halogen group, a cyano group, a nitro group, a hydroxy group, or a carboxy group;
R 30 and R 31 are separate or are linked to each other to form a ring; and
* indicates a binding site to a nitrogen atom or a carbon atom.

6. The compound of claim 1 , wherein the compound represented by Formula 1 is one of the following compounds:

7. An organic light-emitting device, comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode, wherein the organic layer includes the compound of claim 1 .

8. The organic light-emitting device of claim 7 , wherein:
the organic layer includes an emission layer,
the compound represented by Formula 1 is a host or a dopant, and
the device is a fluorescent or phosphorescent device.

9. The organic light-emitting device of claim 7 , wherein the organic layer is a hole injection layer, a hole transport layer, or a functional layer having both hole injection and hole transport capabilities.

10. The organic light-emitting device of claim 7 , wherein:
the organic layer includes at least one of an emission layer, an electron injection layer, an electron transport layer, a functional layer having both electron injection and transport capabilities, a hole injection layer, a hole transport layer, or a functional layer having both hole injection and transport capabilities;
at least one of the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport capabilities further includes the compound represented by Formula 1; and
the emission layer includes an anthracene-based compound, an arylamine-based compound, or a styryl-based compound.

11. The organic light-emitting device of claim 7 , wherein:
the organic layer includes at least one of an emission layer, an electron injection layer, an electron transport layer, a functional layer having both electron injection and transport capabilities, a hole injection layer, a hole transport layer, or a functional layer having both hole injection and transport capabilities;
at least one of the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport capabilities further includes the compound represented by Formula 1; and
the emission layer includes red, green, blue, and white emission layers, at least one of the red, green, blue, or white emission layers including a phosphorescent compound.

12. The organic light-emitting device of claim 11 , wherein at least one of the hole injection layer, the hole transport layer, or the functional layer having both hole injection and hole transport capabilities further includes a charge-generating material.

13. The organic light-emitting device of claim 12 , wherein the charge-gen

Assignees

• Kim Young-Kook
• Hwang Seok-Hwan
• Jung Hye-Jin
• Park Jun-Ha
• Lee Eun-Young
• Lim Jin-O
• Han Sang-Hyun
• Jeong Eun-Jae
• Kim Soo-Yon
• Shin Dae-Yup
• Lee Jong-Hyuk
• Samsung Display Co Ltd

Inventors

• Kim Young-Kook
• Hwang Seok-Hwan
• Jung Hye-Jin
• Park Jun-Ha
• Lee Eun-Young
• Lim Jin-O
• Han Sang-Hyun
• Jeong Eun-Jae
• Kim Soo-Yon
• Shin Dae-Yup
• Lee Jong-Hyuk

Classifications

• C07F7/10

  containing nitrogen {having a Si-N linkage} · CPC title

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D209/88

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D209/86

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