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-12101995-B2
Application number	US-202117208189-A
Country	US
Kind code	B2
Filing date	Mar 22, 2021
Priority date	Sep 29, 2020
Publication date	Sep 24, 2024
Grant date	Sep 24, 2024

Abstract

Provided are an organometallic compound represented by Formula 1, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device:

M(L 1 ) n1 (L 2 ) n2   Formula 1
wherein M, L 1 , L 2 , n1, and n2 in Formula 1 are each the same as described in the present specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:
Formula 1
M(L 1 ) n1 (L 2 ) n2

wherein, in Formula 1,
M is a transition metal,
L 1 is a ligand represented by Formula 2A,
L 2 is a ligand represented by Formula 2B,
n1 and n2 are each independently 1 or 2, wherein, when n1 is 2, two L 1 (s) are identical to or different from each other, and when n2 is 2, two L 2 (s) are identical to or different from each other,
the sum of n1 and n2 is 2 or 3, and
L 1 and L 2 are different from each other:

wherein, in Formulae 2A and 2B,
Y 4 is C or N,
X 21 is O, S, Se, S(═O), or N(R 29 ),
T 1 to T 4 are each independently C, N, carbon bonded to ring CY 1 , or carbon bonded to M in Formula 1, wherein one of T 1 to T 4 is the carbon bonded to M in Formula 1, and one of the remaining groups T 1 to T 4 that is not bonded to M in Formula 1 is the carbon bonded to ring CY 1 ,
T 5 to T 8 are each independently C or N,
ring CY 1 and ring CY 3 are each independently a C 1 -C 30 heterocyclic group,
ring CY 4 is a C 3 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
Z 1 , Z 3 , Z 2 , and Z 4 are each a fluoro group or a fluorinated C 1 -C 20 alkyl group,
a1, a3, and a4 are each independently an integer from 0 to 20, wherein a2 is an integer from 0 to 6, and the sum of a1, a2, a3, and a4 is 1 or more,
R 1 to R 4 and R 29 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 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 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 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -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 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),
b1 and b4 are each independently an integer from 0 to 20, b2 is an integer from 0 to 6, and b3 is an integer from 1 to 20,
when i) none of T 1 to T 8 in Formula 2A is N, ii) a2 in Formula 2A is not 0, and iii) Z 2 in Formula 2A is a fluoro group, then at least one of R 3 (s) in the number of b3 in Formula 2B is —Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 ),
in Formula 2B, and at least one of R 3 (s) in the number of b 3 is —Si(Q 3 )(Q 4 )(Q 5 ), —Ge(Q 3 )(Q 4 )(Q 5 ), or a C 1 -C 20 alkyl group unsubstituted or substituted with at least one deuterium,
two or more of a plurality of R 1 (s) are optionally linked together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more of a plurality of R 2 (s) are optionally linked together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more of a plurality of R 3 (s) are optionally linked together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more of a plurality of R 4 (s) are optionally linked together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
R 10a is the same as described in connection with R 1 ,
* and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 1, and
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 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 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 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted C 2 -C 60 heteroarylalkyl 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, 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 independently substituted with 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 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl 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 heteroarylalkyl 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 a 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 1 -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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Yong Joo
• Kang Byungjoon
• Ishihara Shingo
• Yi Jeoungin
• Choi Byoungki
• Koishikawa Yasushi
• Hwang Kyuyoung

Classifications

• H10K85/342 Primary

  comprising iridium · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/17

  Carrier injection layers · CPC title