Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-9490437-B2
Application number	US-201414568425-A
Country	US
Kind code	B2
Filing date	Dec 12, 2014
Priority date	Sep 26, 2014
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

Abstract

An organometallic compound represented by Formula 1:

M(L 1 ) n1 (L 2 ) n2 ,  Formula 1

wherein M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), and rhodium (Rd), and wherein L 1 is a ligand represented by Formula 2A and L 2 is a ligand represented by Formula 2B, and wherein L 1 and L 2 in Formula 1 are different from each other,

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:
M(L 1 ) n1 (L 2 ) n2 ,   Formula 1

wherein M is iridium (Ir) or platinum (Pt),
wherein L 1 is a ligand selected from substituted and unsubstituted phenylpyridine that coordinates to M via a carbon atom of the phenyl ring and the nitrogen atom of the pyridine ring and L 2 is a ligand represented by Formula 2B, and wherein L 1 and L 2 in Formula 1 are different from each other,

wherein,
CY 3 is a benzene,
R 1 to R 3 in Formula 2B are each independently selected from
a C 1 -C 10 alkyl group; and
a C 1 -C 10 alkyl group, which is substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, —CD 3 , —CF 3 , —CFH, 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, and a C 1 -C 10 alkyl group,

any substituent on L 1 , and R 11 to R 14 in Formula 2B, are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, —SF S , 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 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 having 8to 60 carbon atoms, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group having 1 to 60 carbon atoms, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 ), wherein R 12 in Formula 2B is not a hydrogen, a —CH 3 , or a cyano group; and i) two substituents on the pyridine ring of the L 1 , together with the pyridine ring, optionally form a 5,6,7,8-tetrahydroisoquinoline, and ii) two substituents on the phenyl ring of the L 1 , together with the phenyl ring, optionally form a dibenzofuran, a dibenzothiophene or a carbazole,
and
b1 in Formula 2B is selected from 1, 2, 3, and 4, and

wherein in Formula 1, n1 and n2 are each independently 1 or 2, with the proviso that a sum of n1 and n2 is 2 when M is Pt, or 3 when M is Ir,
wherein * and *′ in Formula 2B are each a binding site to M in Formula 1; and
wherein at least one of substituents 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 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 having 8 to 60 carbon atoms, and the substituted monovalent non-aromatic condensed heteropolycyclic group having 1 to 60 carbon atoms is selected from:
a 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 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 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, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 1 -C 10 cycloalkenyl group, a C 2 -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 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group having 8 to 60 carbon atoms, a monovalent non-aromatic condensed heteropolycyclic group having 1 to 60 carbon atoms, —N(Q 13 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), and —P(═O)(Q 18 )(Q 19 );
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 having 8 to 60 carbon atoms, and a monovalent non-aromatic condensed heteropolycyclic group having 1 to 60 carbon atoms;
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 having 8 to 60 carbon atoms, and a monovalent non-aromatic condensed heteropolycyclic group having 1 to 60 carbon atoms, each substituted with at least one selected from a 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 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 C 1 -C 60 alkyl group, a C 1 -C 60 alkenyl group, a C 1 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 60 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 having 8 to 60 carbon atoms, a monovalent non-aromatic condensed heteropolycyclic group having 1 to 60 carbon atoms, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), and —P(═O)(Q 28 )(Q 29 ); and
—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), and —P(═O)(Q 38 )(Q 39 ),

wherein Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 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 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 aryl group substituted with at least one selected from a C 1 -C 60 alkyl group and a C 6 -C 60

Assignees

• Samsung Electronics Co Ltd

Inventors

• Hwang Kyuyoung
• Kwak Yoonhyun
• Kwon Ohyun
• Kim Soyeon
• Kim Jiwhan
• Lee Sangyeob
• Lee Jungin
• Chung Daeyoung
• Choi Jongwon
• Choi Hyeonho

Classifications

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/185

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