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

Patent metadata

Field	Value
Publication number	US-12018037-B2
Application number	US-201816230529-A
Country	US
Kind code	B2
Filing date	Dec 21, 2018
Priority date	Dec 22, 2017
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

An organometallic compound represented by Formula 1:

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

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode,
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer, and
where the organic layer further comprises at least one organometallic compound represented by Formula 1A(1):

wherein, in Formula 1A(1),
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 and X 4 are each N,
X 2 and X 3 are each C,
a bond between X 1 and M is a coordinate bond, a bond between X 2 and M is a covalent bond, a bond between X 3 and M is a covalent bond, and a bond between X 4 and M is a coordinate bond,
Y 11 is C(Z 11 ), Y 12 is C(Z 12 ), Y 13 is C(Z 13 ), Y 21 is C(Z 21 ), Y 22 is C(Z 22 ), Y 23 is C(Z 23 ), Y 31 is C(Z 31 ), Y 32 is C(Z 32 ), Y 33 is C(Z 33 ), Y 41 is C(Z 41 ), Y 42 is C(Z 42 ), Y 43 is C(Z 43 ), and Y 44 is N,
T 2 is a double bond, *—N(R 5 )—*′, *—B(R 5 )—*′, *—P(R 5 )—*′, *—Si(R 5 )(R 6 )—*′, *—Ge(R 5 )(R 6 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, or *—S(═O) 2 —*′,
Z 11 to Z 13 , Z 21 to Z 23 , Z 31 to Z 33 , Z 41 to Z 43 , R 5 , and R 6 are each independently selected from hydrogen, deuterium, —F, —Cl, —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 7 -C 60 alkyl 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 aryl alkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 00 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl alkyl group, a substituted or unsubstituted C 2 -C 60 alkyl 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 ),
provided that, at least one of Z 1 to Z 13 , Z 21 to Z 23 , Z 31 to Z 33 , and Z 41 to Z 43 is a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 3 -C 60 heteroaryl group, or a combination thereof,
at least two of Z 1 to Z 13 are optionally linked to form a C 5 -C 30 carbocyclic group which is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group which is unsubstituted or substituted with at least one R 10a ,
at least two of Z 21 to Z 23 are optionally linked to form a C 5 -C 30 carbocyclic group which is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group which is unsubstituted or substituted with at least one R 10a ,
at least two of Z 31 to Z 33 are optionally linked to form a C 5 -C 30 carbocyclic group which is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group which is unsubstituted or substituted with at least one R 10a ,
at least two of Z 41 to Z 44 are optionally linked to form a C 5 -C 30 carbocyclic group which is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group which is unsubstituted or substituted with at least one R 10a , and
two of R 5 , R 6 , Z 11 to Z 13 , Z 21 to Z 23 , Z 31 to Z 33 , and Z 41 to Z 43 are optionally linked to form a C 5 -C 30 carbocyclic group which is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group which is unsubstituted or substituted with at least one R 10a ,
R 10a is the same as described in connection with Zn,
* and *′ each indicate a binding site to a neighboring atom,
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 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 7 -C 60 alkyl aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 7 -C 60 aryl alkyl group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted C 2 -C 60 heteroaryl alkyl group, the substituted C 2 -C 60 alkyl 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 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 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 7 -C 60 alkyl aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroaryl alkyl group, a C 2 -C 60 alkyl 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 7 -C 60 alkyl aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroaryl alkyl group, a C 2 -C 60 alkyl heteroaryl group, a monovalent non-aromatic condensed polycyclic grou

Assignees

• Samsung Electronics Co Ltd

Inventors

• Choi Jongwon
• Cho Yongsuk
• Koo Hyun
• Park Bumwoo
• Lee Sunghun
• Ishihara Shingo
• Kwak Yoonhyun
• Kwon Ohyun

Classifications

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K85/324

  comprising aluminium, e.g. Alq3 · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title