Organometallic compounds and organic light-emitting devices comprising the same

Patent metadata

Field	Value
Publication number	US-9748499-B2
Application number	US-201314065285-A
Country	US
Kind code	B2
Filing date	Oct 28, 2013
Priority date	Jun 12, 2013
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

An organometallic compound represented by Formula 1 below is disclosed. An organic light-emitting device including at least one organometallic compound represented by Formula 1 is also disclosed.

First claim

What is claimed is:

1. An organometallic compound, the organometallic compound being represented by Formula 1 below:
Formula 1

wherein, in Formula 1,
R 1 is selected from a substituted or unsubstituted C 6 -C 20 aryl group, and a substituted or unsubstituted C 1 -C 20 heteroaryl group;
a is an integer of 1 to 6, wherein when a is 2 or greater, Formula 1 comprises a plurality of R 1 s, and the R 1 s are identical to or different from each other;
X is a sulfur atom;
R 2 and R 3 are each independently selected from 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 group, a hydrazone group, a carboxylic acid 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 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, and —CO(Q 1 ), Q 1 being a substituted or unsubstituted C 1 -C 30 alkyl group or a substituted or unsubstituted C 6 -C 60 aryl group;
n is an integer of 1 to 3, wherein when n is 2 or greater, Formula 1 comprises a plurality of

s, and each

is identical to or different from each other;
L is an organic ligand; and
m is an integer of 0 to 2, wherein when m is 2, Formula 1 comprises two Ls, and the Ls are identical to or different from each other.

2. The organometallic compound of claim 1 , wherein R 1 is selected from,
a phenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
a phenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one of,
a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, and a C 1 -C 60 alkyl group;
a C 1 -C 60 alkyl group substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group; and
a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 60 alkyl group, a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group.

3. The organometallic compound of claim 1 , wherein R 1 is selected from,
a phenyl group, a naphthyl group, a phenanthryl group, and an anthryl group;
a phenyl group, a naphthyl group, a phenanthryl group, and an anthryl group, each substituted with at least one of,
a deuterium atom, a fluorine atom, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, and a t-butyl group; and
a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, and a t-butyl group, each substituted with at least one of a deuterium atom and a fluorine atom;
a phenyl group, a naphthyl group, a phenanthryl group, and an anthryl group; and
a phenyl group, a naphthyl group, a phenanthryl group, and an anthryl group, each substituted with at least one of a deuterium atom, —F, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, and a t-butyl group.

4. The organometallic compound of claim 1 , wherein R 1 is selected from
a phenyl group; and
a phenyl group substituted with at least one of a deuterium, atom, a fluorine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, and a t-butyl group.

5. The organometallic compound of claim 1 , wherein R 1 is a phenyl group.

6. The organometallic compound of claim 1 , wherein R 2 and R 3 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, 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 1 -C 60 heteroaryl group, and —CO(Q 1 ), Q 1 being selected from a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, and a substituted or unsubstituted carbazolyl group.

7. The organometallic compound of claim 1 , wherein R 2 and R 3 are each independently selected from,
a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, and a nitro group;
a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, and a t-butyl group, each substituted with at least one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, and a nitro group; and
a phenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, each substituted with at least one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a nitro group, a methyl group, and an ethyl group.

8. The organometallic compound of claim 1 , wherein R 2 and R 3 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, and —CF 3 .

Assignees

• Samsung Display Co Ltd
• Pusan Nat Univ Industry-Univ Coop Found

Inventors

• Kim Soung-Wook
• Kim Jae-Hong
• Kim Myeong-Suk
• Lee Moon-Jae
• Jin Sung-Ho

Classifications

• H01L51/0061

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic

• H01L51/0085 Primary

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic