Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-12075693-B2
Application number	US-202016927381-A
Country	US
Kind code	B2
Filing date	Jul 13, 2020
Priority date	Jul 30, 2019
Publication date	Aug 27, 2024
Grant date	Aug 27, 2024

Abstract

An organic light-emitting device includes: a first electrode; a second electrode; an organic layer between the first electrode and the second electrode and including an emission layer; and at least one organometallic compound of the present embodiments. In the organic light-emitting device, the emission layer may further include a host, and the at least one organometallic compound may be a phosphorescent material or a delayed fluorescent material. The organic light-emitting device including the organometallic compound may have a low driving voltage, a high luminance, a high efficiency, and a long lifespan.

First claim

What is claimed is:

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

wherein, in Formula 1, M 1 and M 2 are each independently selected from a first-row transition metal, a second-row transition metal, and a third-row transition metal of the Periodic Table of Elements,
Y 1 to Y 8 are each independently selected from a carbon atom (C) and a nitrogen atom (N),
T 1 to T 8 are each independently selected from a chemical bond, O, S, B(R′), N(R′), P(R′), C(R′)(R″), Si(R′)(R″), Ge(R′)(R″), C(═O), B(R′)(R″), N(R′)(R″), and P(R′)(R″), wherein, when T 1 is a chemical bond, Y 1 and M 1 are directly linked to each other, when T 2 is a chemical bond, Y 2 and M 1 are directly linked to each other, when T 3 is a chemical bond, Y 3 and M 1 are directly linked to each other, when T 4 is a chemical bond, Y 4 and M 1 are directly linked to each other, when T 5 is a chemical bond, Y 5 and M 2 are directly linked to each other, when T 6 is a chemical bond, Y 6 and M 2 are directly linked to each other, when T 7 is a chemical bond, Y 7 and M 2 are directly linked to each other, and when T 8 is a chemical bond, Y 8 and M 2 are directly linked to each other,
two bonds selected from a bond between Y 1 or T 1 and M 1 , a bond between Y 2 or T 2 and M 1 , a bond between Y 3 or T 3 and M 1 , and a bond between Y 4 or T 4 and M 1 are each a coordinate bond, and the other two bonds are each a covalent bond; and two bonds selected from a bond between Y 5 or T 5 and M 2 , a bond between Y 6 or T 6 and M 2 , a bond between Y 7 or T 7 and M 2 , and a bond between Y 8 or T 8 and M 2 are each a coordinate bond, and the other two bonds are each a covalent bond,
ring A 1 is selected from a cyclopentadiene group, a furan group, a thiophene group, and a pyrrole group,
ring A 2 to ring A 9 are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,
X 1 to X 4 are each independently O or S,
L 1 to L 5 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R 10 )(R 11 )—*′, *—C(R 10 )=*′, *═C(R 10 )—*′, *—C(R 10 )═C*(R 11 )*′, *—C(═O)—*′, *—C(═S)—*′, *—B(R 10 )—*′, *—N(R 10 )—*′, *—P(R 10 )(R 11 )—*′, and *—Ge(R 10 )(R 11 )—*′,
a1 to a3 are each independently selected from 0, 1, 2, and 3, wherein at least two of a1 to a3 are each independently selected from 1, 2, and 3,
when a1 is 0, rings A 1 and A 2 are not linked to each other, when a2 is 0, rings A 2 and A 3 are not linked to each other, and when a3 is 0, rings A 1 and A 4 are not linked to each other,
a4 and a5 are each independently selected from 1, 2, and 3,
R′, R″, and R 1 to R 11 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ),
b1 to b9 are each independently an integer from 1 to 20,
any two substituents selected from R 1 to R 11 are optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 carbocyclic group and/or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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;
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 deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
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 condensed heteropolycyclic group;
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 condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an am idino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, 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, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Jaesung
• Kim Sungbum
• Ko Soobyung
• Kim Haejin
• Shin Sujin
• Ahn Eunsoo
• Lee Eunyoung
• Lee Hyunjung
• Jeon Mina
• HAN Junghoon

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K85/361 Primary

  Polynuclear complexes, i.e. complexes comprising two or more metal centers · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11 Primary

  characterised by the electroluminescent [EL] layers · CPC title