Compound for organic light-emitting diode and organic light-emitting diode including the same

Patent metadata

Field	Value
Publication number	US-9567287-B2
Application number	US-201213633850-A
Country	US
Kind code	B2
Filing date	Oct 2, 2012
Priority date	Apr 17, 2012
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

A compound represented by Formula 1 below may be used in an organic light emitting diode. Additionally, in some embodiments, an organic light-emitting diode includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode and including the compound represented by Formula 1.

First claim

What is claimed is:

1. A compound for an organic light-emitting diode represented by Formula 1:

wherein the compound is asymmetric and:
R 1 and R 2 are each independently a halogen, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 3 -C 60 heteroaryl group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group, or R 1 and R 2 optionally combine to form a ring;
R 3 is:
hydrogen,
deuterium,
a halogen,
a cyano group,
an unsubstituted C 6 -C 60 aryl group,
a substituted or unsubstituted C 3 -C 60 heteroaryl group selected from the group consisting of pyrazolyl groups, imidazolyl groups, oxazolyl groups, thiazolyl groups, triazolyl groups, tetrazolyl groups, oxadiazolyl groups, pyridinyl groups, pyridazinyl groups, pyrimidinyl groups, triazinyl groups, indolyl groups, quinolinyl groups, isoquinolinyl groups, and dibenzothiophene groups,
a substituted or unsubstituted C 6 -C 60 condensed polycyclic group, or
a C 6 -C 60 aryl group substituted with a substituent selected from the group consisting of deuterium, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an amidino group, hydrazine, 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 C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 6 -C 16 aryl group, and a C 4 -C 16 heteroaryl group;

Ar 1 and Ar 2 are each independently a moiety represented by any one of Formulae 4a through 4g:

wherein:
Q 1 and Q 2 are each independently a linking group represented by —C(R 30 )(R 31 )—, —N(R 32 )—, —S—, or —O—;
Z 1 , Z 2 , Z 3 , R 30 , R 31 and R 32 are each independently a hydrogen atom, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, an unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group;
p is an integer of 1 to 9;
q is 1 or 2;
r is an integer of 1 to 4; and
* denotes a binding site.

2. The compound of claim 1 , wherein R 1 and R 2 are each independently a halogen, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 3 -C 30 heteroaryl group, or a substituted or unsubstituted C 6 -C 30 condensed polycyclic group;
R 3 is:
hydrogen,
deuterium,
a halogen,
a cyano group,
an unsubstituted C 6 -C 30 aryl group,
a substituted or unsubstituted C 3 -C 30 heteroaryl group selected from the group consisting of pyrazolyl groups, imidazolyl groups, oxazolyl groups, thiazolyl groups, triazolyl groups, tetrazolyl groups, oxadiazolyl groups, pyridinyl groups, pyridazinyl groups, pyrimidinyl groups, triazinyl groups, indolyl groups, quinolinyl groups, isoquinolinyl groups, and dibenzothiophene groups,
a substituted or unsubstituted C 6 -C 30 condensed polycyclic group, or
a C 6 -C 60 aryl group substituted with a substituent selected from the group consisting of deuterium, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an amidino group, hydrazine, 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 C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 6 -C 16 aryl group, and a C 4 -C 16 heteroaryl group.

3. The compound of claim 1 , wherein R 1 and R 2 are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, or a moiety represented by any one of Formulae 2a through 2c:

wherein:
Y 1 , Y 2 , and Y 3 are each independently a linking group represented by —N═, —N(R 20 )—, or —C(R 21 )═;
Q is a linking group represented by —C(R 30 )(R 31 )—, —N(R 32 )—, —S—, or —O—;
Z 1 , Z 2 , R 20 , R 21 , R 30 , R 31 , and R 32 are each independently a hydrogen atom, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, an amino group substituted with a C 6 -C 20 aryl group or a C 3 -C 20 heteroaryl group, a halogen group, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group;
p is an integer of 1 to 7; and
* denotes a binding site.

4. The compound of claim 1 , wherein R 3 is hydrogen, deuterium, a halogen, or a moiety represented by at least one of Formulae 3a through 3c:

wherein:
Y 2 , and Y 3 are each independently a linking group represented by —N═, —N(R 20 )—, or —C(R 21 )═;
Z 1 , Z 2 , R 20 , and R 21 are each independently a hydrogen atom, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group;
p is an integer of 1 to 7; and
* denotes a binding site.

5. The compound of claim 1 , wherein R 1 and R 2 combine to form a ring.

6. A compound for an organic light-emitting diode, wherein the compound is selected from Compounds 1 through 40 and 48 through 50:

7. An organic light-emitting diode comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode, the organic layer comprising the compound according to claim 1 .

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

9. The o

Assignees

• Samsung Display Co Ltd
• Samsung Display Co Ltd

Inventors

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

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07C2103/18

  Chemistry & Metallurgy · mapped topic

• C07D403/14

  containing three or more hetero rings · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title