Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10745422-B2
Application number	US-201514670534-A
Country	US
Kind code	B2
Filing date	Mar 27, 2015
Priority date	May 1, 2014
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

An organometallic compound represented by Formulae 1, 2, or 3 below:

wherein in Formulae 1, 2, and 3, groups and variables are the same as in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formulae 1, 2A, 2B, 2C, or 3:

wherein in Formulae 1, 2A, 2B, 2C, and 3,
M is Al, Ga, Be, Mg, or Zn, provided that M in Formulae 2A, 2B and 2C is Al or Ga;
CY 1 is selected from a pyridine, a pyrazine, a pyrimidine, a pyridazine, a triazine, a quinoline, an isoquinoline, a benzoquinoline, a quinoxaline, a quinazoline, a triazole, an oxazole, a benzooxazole, a benzo[4,5]thieno[2,3-c]pyridine, a benzofuro[2,3-c]pyridine, and a benzoisoquinoline;
CY 2 and CY 21 are each independently a nitrogen-containing heterocyclic group;
provided that when CY 1 is selected from a benzooxazole and a pyridine, CY 2 is selected from a pyridine, a quinoline, and an isoquinoline;
X 1 is N or C,
X 13 is N or CR 13 ,
X 14 is N or CR 14 ,
X 15 is N or CR 15 ,
X 16 is N or CR 16 ,
X 21 is N or CR 21 ,
X 22 is N or CR 22 ,
X 23 is N or CR 23 , and
X 24 is S, O, Si(R 24 )(R 25 ), or N(R 26 );
Z 1 , Z 2 , Z 12 , Z 21 , R 13 to R 16 , and R 21 to R 26 are each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano 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 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -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 2 -C 60 heteroaryl 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 ), or —B(Q 6 )(Q 7 ),
Z 3 is electron withdrawing group;
Z 13 , Z 13a , and Z 13b are each independently selected from —F, a cyano group, a nitro group, a pyridinyl group, a pyrimidinyl group, —CF 3 , and —CF 2 CF 3 ;
a1, a2, and a21 are each independently an integer selected from 0 to 5;
in Formula 2A, a12 is an integer selected from 0 to 2;
in Formulae 2B and 2C, a12 is an integer selected from 0 to 3;
a3 is an integer selected from 1 to 5;
n1 is an integer selected from 1 to 3, provided that n1 in Formulae 2A, 2B and 2C is 3;
L 1 is selected from a monovalent organic ligand, a divalent organic ligand, and a trivalent organic ligand, provided that L 1 in Formulae 2A, 2B and 2C is selected from a halogen ligand, a diketone ligand, a carboxylic acid ligand, a carbon monooxide ligand, an isonitrile ligand, a cyano ligand, and a phosphorous ligand;
n2 is an integer selected from 0 to 3;
provided that
CY 2 in Formula 1 is not a triazine, a pyridazine, or a pyrimidine;
substituents of two adjacent ligands in Formulae 1 and 2A to 2C are not linked to each other;
Z 13 in Formula 2B is not a nitro group;
in Formula 3, when X 24 is N(R 26 ), at least one selected from X 21 to X 23 is N;
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 2 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 2 -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 2 -C 60 heteroaryl group, the substituted a monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from
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 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, 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, 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 2 -C 10 heterocycloalkyl group, a C 3 -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, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 );
a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -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, and a monovalent non-aromatic condensed heteropolycyclic group;
a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -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, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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 2 -C 10 heterocycloalkyl group, a C 3 -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, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ); and
—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), or —B(Q 36 )(Q 37 );
wherein Q 1 to Q 7 , Q 11 to Q 17 , Q 21 to Q 27 , and Q 31 to Q 37 are each independently selected from a hydrogen, 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 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic gro

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Hwang Kyuyoung
• Kwon Ohyun
• Choi Hyeonho
• Kim Changwoo
• Lee Seungjae
• Choi Byoungki

Classifications

• H10K50/00

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F3/02

  Magnesium compounds · CPC title

• C07F5/06 Primary

  Aluminium compounds · CPC title

• C09K2211/104

  with other heteroatoms · CPC title