Organic electroluminescence device and organometallic compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-2025176422-A1
Application number	US-202519030872-A
Country	US
Kind code	A1
Filing date	Jan 17, 2025
Priority date	Dec 15, 2020
Publication date	May 29, 2025
Grant date	—

Abstract

An organic electroluminescence device is provided and including a first electrode, a hole transport region disposed on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer, and a second electrode disposed on the electron transport region, wherein the emission layer may include an organometallic compound, thereby exhibiting high luminous efficiency and long service life characteristics.

First claim

What is claimed is:

1 . A display device, comprising:
a base layer; a circuit layer on the base layer; and a display element layer on the circuit layer and comprising an organic electroluminescence device, wherein the organic electroluminescence device comprises: a first electrode; a second electrode on the first electrode; and an emission layer between the first electrode and the second electrode, and comprising an organometallic compound represented by Formula 1:

wherein, in Formula 1,
M is Pt, Pd, Ni, Au, Ag, Be, Mg, Al, Ca, Ti, Mn, Co, Zn, Ga, Zr, Ru, Rh, or Cu, L 1 is CR 3 R 4 , NR 5 , O, SiR 6 R 7 , BR 8 , or PR 9 ,
X 1 to X 3 are each independently CR 10 or N,
ring A 1 to ring A 3 are each independently a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 ring-forming carbon atoms,
R 1 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
n1 is an integer of 0 to 2,
n2 is an integer of 0 to 4, and
R is represented by Formula 2:

wherein, in Formula 2,
Ar 1 and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
Ar 2 is a substituted or unsubstituted trivalent aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted trivalent heteroaryl group having 2 to 30 ring-forming carbon atoms,
R a to R d are each independently a substituted or unsubstituted amine group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or
R a and R b are bonded to each other to form a ring and/or R c and R d are bonded to each other to form a ring,
provided that, when Ar 2 is a trivalent phenyl group not substituted with any additional substituents, then R a to R d are not all methyl groups at the same time, and
“ ” is the bonding position with Formula 1.

2 . The display device device of claim 1 , wherein Formula 2 is represented by Formula 2-1 or Formula 2-2:

wherein, in Formula 2-1 and Formula 2-2,
R 21 to R 23 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
R a′ to R d′ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, provided that, when n12 is 0, then R a′ to R d′ are not all methyl groups at the same time,
ring B 1 and ring B 2 are each independently a substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, a substituted or unsubstituted hetero cycloalkyl having 2 to 20 carbon atoms, a substituted or unsubstituted bicycloalkyl having 4 to 20 carbon atoms, a substituted or unsubstituted hetero bicycloalkyl having 3 to 20 carbon atoms, a substituted or unsubstituted tricycloalkyl having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero tricycloalkyl having 5 to 20 carbon atoms,
n11 and n13 are each independently an integer of 0 to 5, and
n12 is an integer of 0 to 3.

3 . The display device of claim 2 , wherein ring B 1 and ring B 2 are each independently represented by any one among Formula 3-1 to Formula 3-5:

wherein, in Formula 3-1 to Formula 3-5,
R a1 to R a4 , R b1 to R b5 , R c1 to R c3 , R d1 to R d6 , and R e1 to R e7 are each independently CR 31 R 32 , or NR 33 ,
R 31 to R 32 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
R 33 and R c4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
at least any two groups among R a1 to R a4 , at least any two groups among R b1 to R b5 , at least any two groups among R c1 to R c3 , at least any two groups among R d1 to R d6 , or at least any two groups among R e1 to R e7 are bonded to each other to form bicycloalkyl, hetero bicycloalkyl, tricycloalkyl, or hetero tricycloalkyl, and
n21 is an integer of 0 to 4.

4 . The display device of claim 1 , wherein Formula 1 is represented by Formula 4:

wherein, in Formula 4,
R 24 and R 25 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
n14 and n15 are each independently an integer of 0 to 4, and
L 1 , ring A 3 , R, R 1 , R 2 , n1, and n2 are the same as defined in Formula 1.

5 . The display device of claim 4 , wherein Formula 4 is represented by Formula 5:

wherein, in Formula 5,
R 26 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
n16 is an integer of 0 to 3, and
L 1 , R, R 1 , R 2 , n1, n2, R 24 , R 25 , n14, and n15 are the same as defined in Formula 4.

6 . The display device of claim 1 , wherein the organic electroluminescence device further comprises:
a hole transport region between the first electrode and the emission layer; and an electron transport region between the emission layer and the second electrode.

Assignees

• Samsung Display Co Ltd

Inventors

• Ahn Eunsoo
• Ko Soo-Byung
• Kim Haejin
• Shin Sujin
• Lee Hyunjung
• HAN Junghoon

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/322

  comprising boron · CPC title