Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-2016190484-A1
Application number	US-201514859895-A
Country	US
Kind code	A1
Filing date	Sep 21, 2015
Priority date	Dec 30, 2014
Publication date	Jun 30, 2016
Grant date	—

Abstract

An organometallic compound represented by Formula 1:
M(L 1 ) n1 (L 2 ) n2   Formula 1
wherein in Formula 1, M, L 1 , L 2 , n1, and n2 are the same as described in the specification.

First claim

What is claimed is:

1 . An organometallic compound represented by Formula 1:

wherein M in Formula 1 is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, and Rh;
L 1 in Formula 1 is selected from ligands represented by Formula 2A, and n1 is 1, 2, or 3, wherein when n1 is 2 or more, 2 or more groups L 1 are identical to or different from each other;
L 2 in Formula 1 is selected from a monovalent organic ligand, a divalent organic ligand, a trivalent organic ligand, and a tetravalent organic ligand, and n2 is 0, 1, 2, 3, or 4, wherein when n2 is or more, 2 or more groups L 2 are identical to or different from each other;
L 1 and L 2 in Formula 1 are different from each other;
Y 1 to Y 4 in Formula 2A are each independently C or N, wherein Y 1 and Y 2 are connected to each other via a single bond or a double bond, and Y 3 and Y 4 are connected to each other via a single bond or a double bond;
CY 1 and CY 2 in Formula 2A are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group, wherein CY 1 and CY 2 are optionally connected to each other via a first linking group;
T 1 in Formula 2A is a substituted or unsubstituted C 1 -C 3 alkylene group;
T 2 in Formula 2B is selected from a substituted or unsubstituted C 1 -C 10 alkylene group, a substituted or unsubstituted C 2 -C 10 alkenylene group, a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;
T 3 in Formula 2B is selected from —O—, —S—, a substituted or unsubstituted C 1 -C 7 alkylene group, and a substituted or unsubstituted C 2 -C 7 alkenylene group;
a11 to a 13 in Formulae 2A and 2B are each independently an integer selected from 0 to 3;
R 1 , R 2 , R 11 , and R 12 in Formulae 2A and 2B are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 );
b1 and b2 in Formula 2A are each independently an integer selected from 0 to 4, and c1 in Formula 2B is an integer selected from 0 to 16;
R 13 and R 14 in Formula 2A are each independently the groups of Formula 2B;
b3 and b4 in Formula 2A are each independently an integer selected from 0 to 4, wherein a sum of b3 and b4 (b3+b4) is 1 or more;
* and *′ in Formula 2A each indicates a binding site to M of Formula 1; and
at least one of substituents of the substituted C 1 -C 10 alkylene group, the substituted C 2 -C 10 alkenylene group, the substituted C 3 -C 10 cycloalkylene group, the substituted C 1 -C 10 heterocycloalkylene group, the substituted C 3 -C 10 cycloalkenylene group, the substituted C 1 -C 10 heterocycloalkenylene group, the substituted C 6 -C 60 arylene group, the substituted C 1 -C 60 heteroarylene group, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, 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, and the substituted monovalent non-aromatic condensed heteropolycyclic group 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 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 of 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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, —N(Q 11 )(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, 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, substituted with at least one of 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Jungin
• Kwak Yoonhyun
• Lee Sunyoung
• Kwon Ohyun
• Kwak Seungyeon
• Lee Jiyoun
• Hong Seokhwan
• Jeon Aram

Classifications

• C07F15/0086

  Platinum compounds · CPC title

• C07F15/0033

  Iridium compounds · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L51/5012

  Electricity · mapped topic

• H01L51/0094 Primary

  Electricity · mapped topic