Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-2018090692-A1
Application number	US-201715716263-A
Country	US
Kind code	A1
Filing date	Sep 26, 2017
Priority date	Sep 27, 2016
Publication date	Mar 29, 2018
Grant date	—

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, 2, or 3, wherein when n1 is two or more, two or more 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 0, 1, or 2, wherein when n2 is two or more, two or more 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,
i) when n1 in Formula 1 is three, a) X 2 and X 3 in Formula 2A are N; or b) at least one of X 4 to X 6 in Formula 2A is N, and R 7 is an electron withdrawing group,
ii) when n1 in Formula 1 is one or two, a) at least one of X 3 , X 5 , and X 6 in Formula 2A is N; and b) 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

Assignees

• Samsung Display Co Ltd

Inventors

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

Classifications

• H01L51/5016

  Electricity · mapped topic

• H01L2251/552

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title