Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-11377458-B2
Application number	US-201816161559-A
Country	US
Kind code	B2
Filing date	Oct 16, 2018
Priority date	Oct 16, 2017
Publication date	Jul 5, 2022
Grant date	Jul 5, 2022

Abstract

An organometallic compound represented by Formula 1:M(L1)n1(L2)n2(L3)n3  Formula 1wherein in Formula 1, M, L1, L2, L3, n1, n2, and n3 are the same as defined in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1, M is a transition metal,
in Formula 1, L 1 is a ligand represented by Formula 2,
in Formula 1, n1 is 1, 2, or 3, wherein, when n1 is two or more, two or more of groups L 1 are identical to or different from each other,
in Formula 1, L 2 and L 3 are each independently selected from a monodentate ligand, a bidentate ligand, a tridentate ligand, and a tetradentate ligand,
in Formula 1, n2 and n3 are each independently 0, 1, 2, 3, or 4, wherein, when n2 is two or more, two or more of groups L 2 are identical to or different from each other, and when n3 is two or more, two or more of groups L 3 are identical to or different from each other,
in Formula 2, X 1 is C(R 1 ) or N, X 2 is C(R 2 ) or N, X 3 is C(R 3 ) or N, and X 4 is C(R 4 ) or N,
in Formulae 4A and 4B, X 11 is C(R 11 ) or N, X 12 is C(R 12 ) or N, and X 13 is O, S, Se, N(R 13 ), B(R 13 ), P(R 13 ), or C(R 13 )(R 14 ),
in Formulae 4A and 4B, when X 11 is C(R 11 ) and X 12 is C(R 12 ), R 11 and R 12 are not linked to each other,
in Formulae 4A and 4B, represents a single bond or a double bond,
in Formula 2, i) X 1 is C(R 1 ) and X 2 is C(R 2 ), wherein R 1 and R 2 are linked to each other to form ring CY 2 represented by Formula 4A or 4B, ii) X 2 is C(R 2 ) and X 3 is C(R 3 ), wherein R 2 and R 3 are linked to each other to form ring CY 2 represented by Formula 4A or 4B, or iii) X 3 is C(R 3 ) and X 4 is C(R 4 ), wherein R 3 and R 4 are linked to each other to form ring CY 2 represented by Formula 4A or 4B,
ring CY 1 in Formula 2 and ring CY 2 represented by Formula 4A or 4B are condensed with each other,
a) when X 2 in Formula 2 is C(R 2 ) and X 3 is C(R 3 ), then R 2 and R 3 are linked to each other to form ring CY 2 represented by Formula 4A or 4B, b) when X 13 in Formula 4A and 4B is N(R 13 ), then at least one of X 11 and X 12 in Formula 4A and 4B is N,
in Formula 2,
X 2 is C(R 2 ) and X 3 is C(R 3 ), wherein R 2 and R 3 are linked to each other to form ring CY 2 represented by Formula 4A or 4B, wherein in Formulae 4A and 4B, X 11 is N and X 13 is N(R 13 ), O, or S, or
in Formula 2, X 21 is C or N,
ring CY 21 is i) a first ring, ii) a second ring, iii) a ring in which at least two second rings are condensed with each other, or iv) a ring in which at least one first ring and at least one second rings are condensed with each other,
the first ring is a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isozadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, and a triazasilole group,
the second ring is an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group,
provided that when CY 21 is a ring in which at least one first ring and at least one second rings are condensed with each other, then the at least one second ring is bound to M,
R 1 to R 4 , R 11 to R 14 , and R 21 are each independently selected from hydrogen, 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 ),
a21 is an integer from 0 to 20,
in formula 2, when ring CY 21 is a C 5 -C 30 carbocyclic group, then i) R 21 is selected from —F, —Cl, —Br, —I, —SF 5 , a cyano group, a substituted or unsubstituted C 1 -C 60 alkoxy 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, and ii) a21 is an integer from 1 to 20,
two of a plurality of neighboring groups R 21 are optionally linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
in Formula 2, * and *′ each indicate a binding site to M in Formula 1,
at least one substituent of the substituted C 5 -C 30 carbocyclic group, the substituted C 1 -C 30 heterocyclic 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:
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 selected from 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

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Kim Juhyun
• Kim Wook
• Kwon Youngchun
• Kim Sangmo
• Noh Changho
• Min Minsik
• Park Sangho
• Bae Hyejin
• Oh Wonseok
• Lee Hasup
• Jung Yongsik
• Choi Younsuk

Classifications

• C09K2211/185

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

• C09K11/06

  containing organic luminescent materials · CPC title

• H10K50/12

  comprising dopants · CPC title

• H10K85/342

  comprising iridium · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title