Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10043986-B2
Application number	US-201514680488-A
Country	US
Kind code	B2
Filing date	Apr 7, 2015
Priority date	May 7, 2014
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

An organometallic compound represented by Formula 1:

wherein in Formula 1, M, L 1 , n1, n2, and R 41 to R 47 are described in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1,

wherein
L 1 in Formula 1 comprises at least one selected from a first ligand represented by Formulae 2A-1 to 2A-27 and 2A-29 to 2A-45, a second ligand represented by Formula 2B, and a third ligand represented by one selected from Formulae 2C, 2D, and 2E:

wherein, in Formulae 2 A- 1 to 2 A- 45 ,
Z 1 , Z 2 , Z 11 to Z 13 , and Q 46 to Q 49 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, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, —SF 5 , a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 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, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;
a phenyl group, a naphthyl group, a fluorenyl group, a phenantherenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, an isothizolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a guinolinyl group, an isoguinolinyl group, a benzoguinolinyl group, a guinoxalinyl group, a guinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a guinolinyl group, an isoguinolinyl group, a benzoguinolinyl group, a guinoxalinyl group, a guinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl 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, carboxylic acid group or a salt thereof, squonic acid group or a salt thereof, phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a guinolinyl group, an isoguinolinyl group, a benzoguinolinyl group, a guinoxalinyl group, a guinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;
aa1 is an integer selected from 1 to 4;
ab1 and ab2 are each independently integers selected from 1 to 3;
ac1 and a02 are each independently 1 or 2; and
* and *’are binding sites to M in Formula 1,

in Formulae 1, 2B to 2E, and 3 above,
M is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm;
CY 3 and CY 4 are each independently a C 2 -C 60 heterocyclic group comprising at least one N;
X 1 is N or CR 1 ,
X 2 is N or CR 2 ,
X 3 is N or CR 3 ,
X 4 is N or CR 4 ,
X 11 is N or CR 11 ,
X 12 is N or CR 12 ,
X 13 is N or CR 13 ,
X 14 is N or CR 14 ,
X 15 is N or CR 15 , and
X 16 is N or CR 16 ;
Z 32 is selected from *—O—*′, *—S—*′, *—N(Q 51 )—*′, *—C(Q 52 )(Q 53 )—*′, *—C(Q 54 )═C(Q 55 )—*′, and

b2 is an integer selected from 1 to 10, and when b2 is 2 or greater, groups Z 32 are the same or different;
R 41 to R 47 , Z 3 to Z 6 , R 1 to R 4 , R 11 to R 16 , and Q 51 to Q 59 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, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, —SF 5 , 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

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Noh Changho
• Das Rupasree Ragini
• Lee Kangmun
• Rai Virendra Kumar
• Kravchuk Dmitry

Classifications

• H01L2251/308

  Electricity · mapped topic

• H01L2251/552

  Electricity · mapped topic

• H01L51/0085 Primary

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic