Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10340467-B2
Application number	US-201715830178-A
Country	US
Kind code	B2
Filing date	Dec 4, 2017
Priority date	Jul 9, 2014
Publication date	Jul 2, 2019
Grant date	Jul 2, 2019

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 organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer and at least one organometallic compound represented by Formula 1:

wherein in Formula 1,
M is a Period 3 transition metal;
A 1 ring and A 2 ring are each independently selected from a benzene, a pyridine and a pyrimidine;
A 3 ring and A 4 ring are each independently selected from a benzene, a pyridine, an isoquinoline, a pyrazole, a dibenzofuran and a tetrahydroindazole;
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 a single bond;
Y 1 and Y 3 are each a single bond;
Y 2 is selected from a phenylene group; and
a phenylene group substituted with at least one selected from a deuterium, a methyl group, a tert-butyl group, and a phenyl 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 organic light-emitting device of claim 1 , wherein Y 2 is selected from Formulae 3-1 to 3-3:

wherein in Formulae 3-1 to 3-3,
each of * and *′ indicates a binding site to a neighboring atom.

3. The organic light-emitting device of claim 1 , wherein L 1 is a monodentate ligand, and a1 is 2.

4. The organic light-emitting device of claim 1 , wherein R 1 to R 4 are each independently selected from a hydrogen, 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, —CF 3 , a methoxy group, an ethoxy group, a tert-butoxy group, a phenyl group, —C(═O)(Q 1 ), —Si(Q 1 )(Q 2 )(Q 3 ), and —N(Q 1 )(Q 2 ); and
a phenyl group substituted with a methyl group; wherein R 1 and R 4 or R 2 and R 3 are optionally linked to form a saturated or unsaturated ring; and
Q 1 to Q 3 are each independently selected from 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, and a phenyl group.

5. The organic light-emitting device of claim 1 , wherein R 1 to R 4 are each independently selected from a hydrogen, a deuterium, —F, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, —CF 3 , a methoxy group, a tert-butoxy group, a phenyl group, —C(═O)(CH 3 ), —Si(CH 3 ) 3 , —N(CH 3 ) 2 , —N(Ph) 2 , and a group represented by Formula 4-1; wherein R 1 and R 4 or R 2 and R 3 are optionally linked to form a saturated or unsaturated ring:

wherein in Formula 4-1,
* indicates a binding site to a neighboring atom.

6. The organic light-emitting device of claim 1 , wherein the organometallic compound is represented by any one selected from Formulae 1-1 to 1-8:

wherein in Formulae 1-1 to 1-8,
M, A 1 to A 4 , Y 2 , L 1 , a1, R 1 to R 4 , and b1 to b4 are the same as in Formula 1.

7. The organic light-emitting device of claim 1 , wherein the organometallic compound is represented by any one selected from Formulae 1-1 to 1-8:

Assignees

• Samsung Electronics Co Ltd

Inventors

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

Classifications

• H01L51/0087 Primary

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• H01L51/0081

  Electricity · mapped topic

• C07F15/0026

  without a metal-carbon linkage · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title