Organometallic compound, organic light-emitting device including the same and electronic apparatus including the organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12063850-B2
Application number	US-202017060751-A
Country	US
Kind code	B2
Filing date	Oct 1, 2020
Priority date	Dec 24, 2019
Publication date	Aug 13, 2024
Grant date	Aug 13, 2024

Abstract

An organometallic compound, wherein the organometallic compound has a C 2 symmetric structure, and is represented by Formula 1,
wherein the sum of Δ(Ir—N) and Δ(Ir—C) is about 0.002 angstroms or less:

Ir(L 1 ) 2 (L 2 )  Formula 1
wherein, in Formula 1, L 1 is a ligand represented by Formula 2 as provided herein, wherein one of two L 1 s is a first L 1 ligand and the other L 1 s is a second L 1 ligand and the first L 1 ligand and the second L 1 ligand are identical to each other, L 2 is a ligand represented by Formula 3 as provided herein, and Δ(Ir—N) and Δ(Ir—C) are as defined herein.

First claim

What is claimed is:

1. An organometallic compound, wherein the organometallic compound has a C 2 symmetric structure, and is represented by Formula 1,
wherein a sum of Δ(Ir—N) and Δ(Ir—C) is 0.002 angstroms or less:
Ir(L 1 ) 2 (L 2 )  Formula 1

wherein, in Formula 1,
L 1 is a ligand represented by Formula 2, wherein one of two L 1 s is a first L 1 ligand and the other L 1 s is a second L 1 ligand, and the first L 1 ligand and the second L 1 ligand are identical to each other, and
L 2 is a ligand represented by Formula 3,

wherein, in Formula 2,
Y 1 is N, and Y 2 is C,
ring CY 1 is a polycyclic group comprising three or more 6-membered rings that are condensed with each other,
ring CY 2 is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
T 1 is a group having a para Hammett substituent constant (σ p ) that is greater than 0 and less than 0.5,
b1 is an integer from 1 to 10, wherein, when b1 is 2 or more, two or more T 1 groups are identical to or different from each other,
R 1 , R 2 and R 31 to R 33 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroarylalkyl group, a substituted or unsubstituted C 2 -C 60 alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),
a1 and a2 in Formula 2 are each independently an integer from 0 to 10, wherein, when a1 is 2 or more, two or more R 1 groups are identical to or different from each other, and when a2 is 2 or more, two or more R 2 groups are identical to or different from each other,
* and *′ in Formulae 2 and 3 each indicate a binding site to Ir in Formula 1,
Δ(Ir—N) is an absolute value of a difference between an Ir and Y 1 bond distance for the first L 1 ligand and an Ir and Y 1 bond distance for the second L 1 ligand in Formulae 1 and 2,
Δ(Ir—C) is an absolute value of a difference between an Ir and Y 2 bond distance for the first L 1 ligand and an Ir and Y 2 bond distance for the second L 1 ligand in Formulae 1 and 2,
two or more of R 1 groups in the number of a1 are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or two or more of R 1 groups in the number of a1 are optionally linked to each other to form a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
two or more of R 2 groups in the number of a2 are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or two or more of R 2 groups in the number of a2 are optionally linked to each other to form a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
two or more of R 1 and R 2 are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or two or more of R 1 and R 2 are optionally linked to each other to form a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
two or more of R 31 to R 33 are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or two or more of R 31 to R 33 are optionally linked to each other to form a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
R 1a is the same as defined in connection with R 1 , and
a substituent of 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 7 -C 60 arylalkyl group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted C 2 -C 60 heteroarylalkyl group, the substituted C 2 -C 60 alkylheteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is each independently:
deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro 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, or 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, or a C 1 -C 60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro 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 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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a C 2 -C 60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or a combination thereof;
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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —C

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kwak Seungyeon
• Aratani Sukekazu
• Kim Sangdong
• Choi Hyeonho
• Koo Hyun
• Kim Soyeon
• Lee Jiyoun
• Cho Yongsuk
• Choi Jongwon
• Kravchuk Dmitry

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title