Novel organometallic compounds and organic light emitting diode including same

Patent metadata

Field	Value
Publication number	US-2023045531-A1
Application number	US-202217845406-A
Country	US
Kind code	A1
Filing date	Jun 21, 2022
Priority date	Jun 24, 2021
Publication date	Feb 9, 2023
Grant date	—

Abstract

Disclosed herein are a novel organometallic compound and an organic light-emitting diode including same. More specifically, an organometallic compound represented by [Chemical Formula 1] and an organic light-emitting diode including same are provided.

First claim

1 . The present disclosure aims to provide an organometallic compound represented by the following Chemical Formula 1:

wherein,
L 1 is selected from a substituted or unsubstituted 5-membered heteroaromatic ring, a substituted or unsubstituted 5-membered heteroaliphatic ring, and a substituted or unsubstituted 5-membered N-heterocyclic carbene,
Y is C or N,
Z is C or N,
X 1 to X 3 , which are same or different, are each independently any one selected from CR 1 R 2 , CR 3 , NR 4 , N, O, S, and Se,
wherein when two or more of X1 to X3 are CR1R2, the plural CR1R2 radicals may be same or different, when two or more of X1 to X3 are CR3, the plural CR3 radicals may be same or different, and when two or more of X1 to X3 are NR4, the plural NR4 radicals may be same or different,
R 1 to R 4 , which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused heterocycloalkyl of 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 8 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaryl of 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy of 6 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 30 carbon atoms, a substituted or unsubstituted silyl of 0 to 30 carbon atoms, a substituted or unsubstituted germyl of 0 to 30 carbon atoms, a nitro, a cyano, and a halogen, and
any adjacent two substituents of X 1 to X 3 can be optionally linked to each other to additionally form a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, a substituted or unsubstituted heteroaromatic ring of 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring of 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaliphatic ring of 3 to 30 carbon atoms,
L 2 is selected from a substituted or unsubstituted 5-membered heteroaromatic ring, and a substituted or unsubstituted 5-membered heteroaliphatic ring,
X 5 to X 7 , which are same or different, are each independently any one selected from CR 5 R 6 , CR 7 , NR 8 , N, O, and S,
wherein when two or more of X 5 to X 7 are CR 5 R 6 , the plural CR 5 R 6 radicals may be same or different, when two or more of X 5 to X 7 are CR 7 , the plural CR 7 radicals may be same or different, and when two or more of X 5 to X 7 are NR 8 , the plural NR 8 radicals may be same or different,
R 5 to R 8 , which are same or different, are each independently as defined above for R 1 to R 4 , respectively, and
any adjacent two substituents of X 5 to X 7 can be optionally linked to each other to additionally form a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, a substituted or unsubstituted heteroaromatic ring of 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring of 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaliphatic ring of 3 to 30 carbon atoms,
L 3 and L 4 , which are same or different, are each independently selected from a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring of 5 to 50 carbon atoms, a substituted or unsubstituted fused ring of 7 to 50 carbon atoms with an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring fused to each other, a substituted or unsubstituted heteroaromatic ring of 2 to 50 carbon atoms, and a substituted or unsubstituted fused ring of 6 to carbon atoms with an heteroaromatic ring and an aliphatic hydrocarbon ring fused to each other,
wherein L 4 can be bonded to at least adjacent one of R 5 to R 8 in X 7 to form an additional condensed ring,
T is a linker selected from CR 9 R 10 , SiR 11 R 12 , NR 13 , BR 14 , PR is , R 16 P═O, GeR 17 R 18 , O, and S,
wherein R 9 to R 18 , which are same or different, are each independently as defined above for R 1 to R 4 , respectively,
wherein the term “substituted” in the expression “substituted or unsubstituted” used for the compound of Chemical Formula 1 means having at least one substituent selected from the group consisting of a deuterium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, cycloalkyl of 3 to 30 carbon atoms, an alkenyl of 2 to 24, an alkynyl of 2 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 2 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an amine of 1 to 24 carbon atoms, a silyl of 1 to 24 carbon atoms, a germyl of 1 to 24 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arythionyl of 6 to 24 carbon atoms.

2 . The organometallic compound of claim 1 , wherein the L 1 is a substituted or unsubstituted 5-membered N-heterocyclic carbene.

3 . The organometallic compound of claim 1 , wherein
L 1 in Chemical Formula 1 may have a structure represented by any one selected from the following Structural Formulas 1 to 4:

wherein,
R and R′, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused heterocycloalkyl of 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 8 to 30 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaryl of 5 to 30 carbon atoms,
n is an integer of 1 to 3 wherein when n is 2 or higher, the corresponding R's are same or different and the adjacent R's can be linked to each other to additionally form a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, a substituted or unsubstituted heteroaromatic ring of 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring of to 30 carbon atoms, or a substituted or unsubstituted heteroaliphatic ring of 3 to 30 carbon atoms,
“-*” stands for a single bond to the L 3 ring

Assignees

• Sfc Co Ltd

Inventors

• Lee Chun-Young
• Kim Hak-Kyu
• Kim Tae-Young

Classifications

• C07B59/004

  Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K85/346 Primary

  comprising platinum · CPC title

• H10K2101/30

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

• H10K50/12

  comprising dopants · CPC title