Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-12137604-B2
Application number	US-202017036088-A
Country	US
Kind code	B2
Filing date	Sep 29, 2020
Priority date	Dec 20, 2019
Publication date	Nov 5, 2024
Grant date	Nov 5, 2024

Abstract

Provided are an organometallic compound represented by Formula 1 and an organic light-emitting device including the same:wherein, in Formula 1, Y1, Y2, Xa, Xb, ring CY1, ring CY2, R1, R2, A1 to A7, a1, and a2 are as defined in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1, Y 1 is N, Y 2 is C, and ring CY 1 is a group represented by Formula 1-1 or 1-2,

in Formulae 1, 1-1 and 1-2, ring CY 2 , ring CY 11 and ring CY 12 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
in Formula 1, X a is N or C(T a ), and X b is N or C(T b ),
in Formula 1-1, X 1 is N or C(R 11 ), and X 2 is N or C(R 12 ),
in Formulae 1-1 and 1-2, * and *′ are condensation sites to the adjacent 6-membered ring of Formula 1,
a group represented by

 is a group represented by one of Formulae 3-1 to 3-36 and 3-38 to 3-48:

wherein, in Formulae 3-1 to 3-36 and 3-38 to 3-48,
X a is C(T a ), and X b is C(T b ), or X a is N and X b is N,
a19 is an integer of 0 to 12,
a18 is an integer of 0 to 8,
a17 is an integer of 0 to 7,
a16 is an integer of 0 to 6,
a15 is an integer of 0 to 5,
a14 is an integer of 0 to 4,
* is a binding site to Ir in Formula 1, and
*″ is a binding site to an adjacent atom in Formula 1,
in Formulae 1, R 1 , R 2 , T a , T b , and A 1 to A 7 are each independently 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 2 -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 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),
R 11 and R 12 are the same as defined above in connection with R 1 ,
a1 is an integer of 1 to 20, and when a1 is 2 or greater, two or more of R 1 (s) are identical to or different from each other,
a2 is an integer of 0 to 20, and when a2 is 2 or greater, two or more of R 2 (s) are identical to or different from each other,
at least one of R 1 (s) in number of a1 is 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 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
two or more of R 1 (s) in number of a1 are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
two or more of R 2 (s) in number of a2 are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
R 1 and R 2 are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
two or more of A 1 to A 7 are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
R 1a is the same as defined in connection with A 7 ,
a 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 2 -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:
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 or 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, or a C 1 -C 60 alkoxy group, each substituted with deuterium, —F, —C 1 , —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 2 -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 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or any combination thereof;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -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 mo

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kim Soyeon
• Kwon Ohyun
• Lee Jiyoun
• Cho Yongsuk
• Choi Jongwon
• Kravchuk Dmitry
• Kwak Seungyeon
• Sim Myungsun
• Lee Sunghun

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C09K2211/185

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

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title