Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound

Patent metadata

Field	Value
Publication number	US-10937973-B2
Application number	US-201715641299-A
Country	US
Kind code	B2
Filing date	Jul 4, 2017
Priority date	Jul 5, 2016
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

An organometallic compound represented by Formula 1A:

wherein, in Formula 1A, groups and variables are the same as described in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1A:

wherein, in Formula 1A,
M is beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au),
X 1 is O or S, and a bond between X 1 and M is a covalent bond,
X 2 and X 3 are each independently C or N,
X 4 is N,
one bond selected from a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a covalent bond, and the others thereof are each a coordinate bond,
Y 1 and Y 3 to Y 5 are each independently C or N,
a bond between X 2 and Y 3 , a bond between X 2 and Y 4 , a bond between Y 4 and Y 5 , a bond between Y 5 and X 51 , a bond between X 51 and Y 3 are each a chemical bond,
CY 1 to CY 5 are each independently selected from a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group, wherein CY 4 is not a benzimidazole group,
a cyclometallated ring formed by CY 5 , CY 2 , CY 3 , and M is a 6-membered ring,
X 51 is selected from O, S, N-[(L 7 ) b7 -(R 7 ) c7 ], C(R 7 )(R 8 ), Si(R 7 )(R 8 ), Ge(R 7 )(R 8 ), C(═O), N, C(R 7 ), Si(R 7 ), and Ge(R 7 ),
R 7 and R 8 are optionally linked via a first linking group to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
L 1 to L 4 and L 7 are each independently selected from a substituted or unsubstituted C 5 -C 30 carbocyclic group and a substituted or unsubstituted C 1 -C 30 heterocyclic group,
b1 to b4 and b7 are each independently an integer from 0 to 5,
R 1 to R 4 , R 7 , and R 8 are each independently selected from hydrogen, deuterium, —F, —C, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro 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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl 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 ),
c1 to c4 are each independently an integer from 1 to 5,
c7 is 1,
a1 to a4 are each independently 0, 1, 2, 3, 4, or 5, two of a plurality of neighboring groups R 1 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
two of a plurality of neighboring groups R 2 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
two of a plurality of neighboring groups R 3 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
two of a plurality of neighboring groups R 4 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
two or more neighboring groups selected from R 1 to R 4 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
provided that, in cases where i) to viii) apply, a1 to a4 are each independently 1, 2, 3, 4, or 5, and at least one selected from R 1 to R 4 is selected from 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
i) M is Pt, ii) X 1 is O, iii) X 2 and X 4 are each N, X 3 is C, a bond between X 2 and M and a bond between X 4 and M are each a coordinate bond, and a bond between X 3 and M is a covalent bond, iv) Y 1 to Y 5 are each C, v) a bond between Y 5 and X 51 and a bond between Y 3 and X 51 are each a single bond, vi) CY 1 , CY 2 , and CY 3 are each a benzene group, and CY 4 is a pyridine group, vii) X 51 is O, S, or N-[(L 7 ) b7 -(R 7 ) c7 ], and viii) b7 is 0, c7 is 1, and R 7 is a substituted or unsubstituted C 1 -C 60 alkyl group,
provided that when i) M is Pt, ii) X 1 is O, iii) X 2 and X 4 are each N, X 3 is C, a bond between X 2 and M and a bond between X 4 and M are each a coordinate bond, and a bond between X 3 and M is a covalent bond, iv) Y 1 to Y 5 are each C, v) a bond between Y 5 and X 51 and a bond between Y 3 and X 51 are each a single bond, vi) CY 1 , CY 2 , and CY 3 are each a benzene group, and CY 4 is a pyridine group, vii) X 51 is O, S, or NH, viii) b1, b2, c1, and c2 are each O, and ix) R 1 , R 2 , and R 4 are each hydrogen, then R 3 is not tert-butyl;
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 7 -C 60 arylalkyl group, the substituted C 1 -C 60 heteroaryl group, the substituted C 2 -C 60 heteroaryloxy group, the substituted C 2 -C 60 heteroarylthio group, the substituted C 3 -C 60 heteroarylalkyl 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 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, C 1 -C 60 alkyl group, a C 2 -C 60 a

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Jungin
• Hwang Kyuyoung
• Kim Soyeon
• Jeon Aram
• Choi Hyeonho
• Koo Hyun
• Kim Sangdong
• Kwak Yoonhyun
• Kwon Ohyun
• Choi Byoungki

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

• C07F15/0086 Primary

  Platinum compounds · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title