Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10916714-B2
Application number	US-201715716263-A
Country	US
Kind code	B2
Filing date	Sep 26, 2017
Priority date	Sep 27, 2016
Publication date	Feb 9, 2021
Grant date	Feb 9, 2021

Abstract

An organometallic compound and an organic light-emitting device including the same are provided. The organometallic compound may be represented by Formula 1, wherein L 1 is a ligand represented by Formula 2A and L 2 is a ligand represented by Formula 2B. Further details about the compounds are presented in the disclosure.

M(L 1 ) n1 (L 2 ) n2 ,  <Formula 1>
wherein M is iridium.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein M in Formula 1 is iridium (Ir),
in Formula 1, L 1 is a ligand represented by Formula 2A and n1 is 1 or 2, wherein when n1 is two, two L 1 (s) are identical to or different from each other,
in Formula 1, L 2 is a ligand represented by Formula 2B and n2 is 1 or 2, wherein when n2 is two, two L 2 (s) are identical to or different from each other,
the sum of n1 and n2 in Formula 1 is three,
* and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 1,
in Formula 2A, X 1 is N or C(R 1 ), X 2 is N or C(R 2 ), X 3 is N or C(R 3 ), X 4 is N or C(R 4 ), X 5 is N or C(R 5 ), and X 6 is N or C(R 6 ),
in Formula 2B, Y 1 is C, Y 2 and Y 3 is each independently C or N, Y 4 is N, a bond between Y 1 and Y 2 is a single bond or a double bond, a bond between Y 2 and Y 3 is a single bond, and a bond between Y 3 and Y 4 is a single bond or a double bond,
in Formula 2B, ring A 1 is a C 4 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group and ring A 2 is a C 1 -C 60 heterocyclic group,
R 1 to R 7 , R 11 , and R 12 in Formulae 2A and 2B 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 hydrazone 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 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
any two neighboring groups selected from R 1 to R 7 in Formula 2A are optionally linked to form a substituted or unsubstituted C 4 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
any two neighboring groups selected from two or more R 11 (s) in Formula 2B are optionally linked to form a substituted or unsubstituted C 4 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
any two neighboring groups selected from two or more R 12 (s) in Formula 2B are optionally linked to form a substituted or unsubstituted C 4 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
neighboring R 11 and R 12 in Formula 2B are optionally linked to form a substituted or unsubstituted C 4 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
a11 and a12 in Formula 2B are each independently 0, 1, 2, 3, 4, or 5,
at least one of X 5 and X 6 in Formula 2A is N,
X 1 in Formula 2A is C(R 1 ), X 4 is C(R 4 ), and at least one of R 1 and R 4 is an electron withdrawing group, and
at least one 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 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C 4 -C 60 carbocyclic group, and the substituted C 1 -C 60 heterocyclic group is selected from:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone 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 hydrazone 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 amidino group, a hydrazino group, a hydrazone 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 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ), and
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ),
wherein Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 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 hydrazone 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C 1 -C 60 alkyl group substituted

Assignees

• Samsung Display Co Ltd

Inventors

• Kang Sunwoo
• Jeon Sangho
• Cho Youngmi
• Ko Soobyung
• Kim Taekyung

Classifications

• H10K2101/40

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/185

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