Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device

Patent metadata

Field	Value
Publication number	US-2025089551-A1
Application number	US-202418824412-A
Country	US
Kind code	A1
Filing date	Sep 4, 2024
Priority date	Sep 4, 2023
Publication date	Mar 13, 2025
Grant date	—

Abstract

An organometallic compound represented by Formula 1:

wherein M 1 is a transition metal; Y 1 to Y 3 are each independently C or N; R 4 is a substituted or unsubstituted C 1 -C 60 alkyl group; ring CY 2 to ring CY 5 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group; L 1 is a single bond, O, S, Se, N(R 61 ), B(R 61 ), C(R 61 )(R 62 ), or Si(R 61 )(R 62 ); a1 is 1, 2, 3, 4, or 5; b10, b20, b30, b40, and b50 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and the remaining substituent groups of Formula 1 are as provided herein.

First claim

What is claimed is:

1 . An organometallic compound, represented by Formula 1:

wherein, in Formula 1,
M 1 is a transition metal,
Y 1 to Y 3 are each independently C or N,
ring CY 2 to ring CY 5 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
X 6 is C(R 6 ) or N, X 7 is C(R 7 ) or N, and X 8 is C(R 8 ) or N,
X 9 is C(R 9 ) or N, X 10 is C(R 10 ) or N, X 11 is C(R 11 ) or N, and X 12 is C(R 12 ) or N,
X 13 is C(R 13 ) or N, X 14 is C(R 14 ) or N, X 15 is C(R 15 ) or N, and X 16 is C(R 16 ) or N,
X 17 is C(R 17 ) or N, X 18 is C(R 18 ) or N, and X 19 is C(R 19 ) or N,
L 1 is a single bond, O, S, Se, N(R 61 ), B(R 61 ), C(R 61 )(R 62 ), or Si(R 61 )(R 62 ),
a1 is 1, 2, 3, 4, or 5,
R 4 is a substituted or unsubstituted C 1 -C 60 alkyl group,
R 1 to R 3 , R 5 to R 20 , R 30 , R 40 , R 50 , R 61 , and R 62 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 hydrazino group, a hydrazono 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 1 -C 60 alkylthio 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 7 -C 60 aryl alkyl 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 C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl alkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —Ge(Q 1 )(Q 2 )(Q 3 ), —C(Q 1 )(Q 2 )(Q 3 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —N(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(Q 8 )(Q 9 ), —P(═O)(Q 8 )(Q 9 ), or —P(═S)(Q 8 )(Q 9 ),
neighboring two or more of R 1 to R 20 , R 30 , R 40 , R 50 , R 61 , and R 62 are optionally bonded 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,
b20, b30, b40, and b50 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10,
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 1 -C 60 alkylthio 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 7 -C 60 aryl alkyl 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 C 2 -C 60 alkyl heteroaryl group, the substituted C 2 -C 60 heteroaryl alkyl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, —SF 5 , —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, a C 1 -C 60 alkoxy group, or a C 1 -C 60 alkylthio group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, or a C 1 -C 60 alkylthio group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF 5 , —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 1 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 alkyl aryl group, a C 7 -C 60 aryl alkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —Ge(Q 11 )(Q 12 )(Q 13 ), —C(Q 11 )(Q 12 )(Q 13 ), —C(═O)(Q 11 ), —S(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —N(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(Q 18 )(Q 19 ), —P(═O)(Q 18 )(Q 19 ), —P(═S)(Q 18 )(Q 19 ), or a combination thereof;
a C 3 -C 10 cycloalkyl group, a C 1 -C 1 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 1 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 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or 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 7 -C 60 alkyl aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF 5 , —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, a C 1 -C 60 alkoxy group, a C 1 -C 60 alkylthio 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 7 -C 60 alkyl aryl group, a C 7 -C 60 aryl alkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kim Hwang Suk
• Kim Sangmo
• Min Minsik
• Bae Hyejin
• Chung Yeon Sook
• Choi Hyesung
• Heo Joon
• Kang Hosuk
• Kim Jong Soo
• Kim Joonghyuk
• Son Youngmok
• Lee Yeonkyung
• Jeong Daun
• Ju Kyeongsik

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/185

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

• H10K50/121

  for assisting energy transfer, e.g. sensitization · CPC title

• H10K85/346 Primary

  comprising platinum · CPC title