Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-2016013431-A1
Application number	US-201414579499-A
Country	US
Kind code	A1
Filing date	Dec 22, 2014
Priority date	Jul 9, 2014
Publication date	Jan 14, 2016
Grant date	—

Abstract

An organometallic compound of Formula 1:

wherein in Formula 1, groups and variables are as described in the specification.

First claim

What is claimed is:

1 . An organometallic compound represented by Formula 1:

wherein in Formula 1,
M is selected from a Period 1 transition metal, a Period 2 transition metal, and a Period 3 transition metal;
A 1 ring to A 4 ring are each independently selected from a C 6 -C 20 carbocyclic group and a C 1 -C 20 heterocyclic group, provided that each of A 3 ring and A 4 ring is not simultaneously a benzene;
X 1 to X 4 are each independently selected from C and N;
B 1 to B 4 are each independently selected from a single bond, O, and S;
Y 1 and Y 3 are each independently selected from a single bond and a divalent linking group;
Y 2 is selected from a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group;
L 1 is selected from a monodentate ligand and a bidentate ligand;
a1 is selected from 0, 1, and 2;
R 1 to R 4 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid 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 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, —C(═O)(Q 1 ), —Si(Q 1 )(Q 2 )(Q 3 ), and —N(Q 1 )(Q 2 ); wherein R 1 and R 4 or R 2 and R 3 are optionally linked to form a saturated or unsaturated ring;
Q 1 to Q 3 are each independently selected from a C 1 -C 60 alkyl group and a C 6 -C 60 aryl group;
b1 to b4 are each independently selected from 1, 2, 3, and 4; and
at least one substituent of the substituted C 6 -C 60 arylene group, substituted C 1 -C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic hetero-condensed polycyclic group, the substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 1 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 1 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 1 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic hetero-condensed polycyclic group is selected from
a deuterium, —F, —Cl, —Br, —I, 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 C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, 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; and
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group;

2 . The organometallic compound of claim 1 , wherein M is a Period 3 transition metal.

3 . The organometallic compound of claim 1 , wherein A 1 ring to A 4 ring are each independently selected from a benzene, a naphthalene, a pyrrole, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, a triazole, indazole, tetrahydroindazole, a pyridine, a pyrimidine, a pyrazine, a pyridazine, a triazine, a quinoline, an isoquinoline, a dibenzofuran, and a dibenzothiophene.

4 . The organometallic compound of claim 1 , wherein A 1 ring to A 4 ring are each independently selected from a benzene, a pyrazole, an indazole, a tetrahydroindazole, a pyridine, a quinoline, an isoquinoline, and a dibenzofuran.

5 . The organometallic compound of claim 1 , wherein each of B 1 to B 4 is a single bond.

6 . The organometallic compound of claim 1 , wherein Y 1 and Y 3 are each independently selected from a single bond, —O—, —S—, —{B(Q 11 )}-, —{N(Q 12 )}-, —{C(Q 11 )(Q 12 )} n1 -, —{Si(Q 11 )(Q 12 )} n1 -, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group;
Q 11 and Q 12 are each independently selected from a hydrogen, a deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group; and
n1 is selected from 1, 2, and 3.

7 . The organometallic compound of claim 1 , wherein Y 1 and Y 3 are each independently selected from a single bond, —O—, —S—, —{B(Q 11 )}-, —{N(Q 11 )}-, —{C(Q 11 )(Q 12 )} n1 -, —{Si(Q 11 )(Q 12 )} n1 -, a phenylene group, a naphthylene group, a fluorenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a quinolinylene group, an isoquinolinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a quinolinylene group, an isoquinolinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a phenyl group, and a pyridinyl group;
Q 11 and Q 12 are each independently selected from a hydrogen, a deuterium, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, and a phenyl group; and
n1 is 1.

Assignees

• Samsung Electronics Co Ltd

Inventors

• Choi Jongwon
• Kwak Seungyeon
• Kwak Yoonhyun
• Kwon Ohyun
• Kim Jiwhan
• Lee Kumhee
• Lee Sunyoung

Classifications

• H01L51/5024

  Electricity · mapped topic

• C07D401/14

  containing three or more hetero rings · CPC title

• H01L51/0088

  Electricity · mapped topic

• C07F15/0086

  Platinum compounds · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title