Organic electroluminescence device and organometallic compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-12426496-B2
Application number	US-202117541130-A
Country	US
Kind code	B2
Filing date	Dec 2, 2021
Priority date	Mar 25, 2021
Publication date	Sep 23, 2025
Grant date	Sep 23, 2025

Abstract

An organic electroluminescence device 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 represented by Formula 1 to thereby exhibit a long service life and/or high efficiency:

First claim

What is claimed is:

1. An organic electroluminescence device comprising:
a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the emission layer comprises an organometallic compound represented by Formula 1:

wherein, in Formula 1,
M is Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, or Os,
ring A1 to ring A7 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 1 to 60 ring-forming carbon atoms,
L 1 and L 2 are each independently a direct linkage, *—O—*′, *—S—*′, *—C(R 11 )(R 12 )—*′, *—C(R 13 )═*′, *═C(R 14 )—*′, *—C(R 15 )═C(R 16 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 17 )—*′, *—N(R 18 )—*′, *—P(R 19 )*′, *—Si(R 20 )(R 21 )—*′, *—P(R 22 )(R 23 )—*′, or *—Ge(R 24 )(R 25 )*′,
R 11 to R 25 are each independently a hydrogen atom, a deuterium atom, 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, and/or are bonded to an adjacent group to form a ring,
R 1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine 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, and n1 and n2 are each independently an integer of 0 to 3, and
wherein when M is Pt or Pd, L 1 is O, n1 is 1, A1, A2, A5 and A6 are each a benzene ring, and A7 is a 5-membered ring, then A5 and A6 are each substituted with one or more substituents selected from a tert-butyl group, a cyano group, an amine group, a substituted or unsubstituted oxy 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.

2. The organic electroluminescence device of claim 1 , wherein ring A1 to ring A7 are each independently a pentagonal ring, a hexagonal ring, or a heptagonal ring.

3. The organic electroluminescence device of claim 1 , wherein the emission layer is to emit phosphorescence.

4. The organic electroluminescence device of claim 1 , wherein the emission layer further comprises a host, and
the organometallic compound represented by Formula 1 is a dopant.

5. The organic electroluminescence device of claim 1 , wherein the organometallic compound represented by Formula 1 is represented by Formula 2:

and
wherein, in Formula 2,
R 2 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine 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,
a and b are each independently an integer of 0 to 3,
c is an integer of 0 to 2,
L 3 is a direct linkage, *—O—*, *—S—*′, *—C(R 26 )(R 27 )—*′, *—C(R 28 )═*′, *═C(R 29 )—*′, *—C(R 30 )═C(R 31 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R 32 )—*′, *—N(R 33 )—*′, *—P(R 34 )—*′, *—Si(R 35 )(R 36 )—*′, *—P(R 37 )(R 38 )—*′, or *—Ge(R 39 )(R 40 )—*′,
R 26 to R 40 are each independently a hydrogen atom, a deuterium atom, 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, and/or are bonded to an adjacent group to form a ring,
n3 is an integer of 0 to 3, and
M, ring A4 to ring A6, R 1 , L 1 , L 2 , n1 and n2 are each independently the same as defined in Formula 1.

6. The organic electroluminescence device of claim 5 , wherein the organometallic compound represented by Formula 2 is represented by Formula 3:

wherein, in Formula 3,
R 5 and R 6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy group, an amine 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,
d and e are each independently an integer of 0 to 4, and
M, ring A4, R 1 to R 4 , a to c, L 1 to L 3 , and n1 to n3 are each independently the same as defined in Formula 2, and
wherein when M is Pt or Pd, L 1 is O, n1 is 1, and n3 is 0, then d and e are each an integer of 1 to 4, and R 5 and R 6 are each independently a tert-butyl group, a cyano group, an amine group, a substituted or unsubstituted oxy 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.

7. The organic electroluminescence device of claim 6 , wherein the organometallic compound represented by Formula 3 is represented by any one among Formula 4-1 to Formula 4-3:

wherein, in Formula 4-1 to Formula 4-3,
L 3 is *—O—*′, *—S—*′, *—C(R 26 )(R 27 )—*′, or N(R 33 )—*′,
R 26 , R 27 , and R 33 are each independently a hydrogen atom, a deuterium atom, 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, and/or are bonded to an adjacent group to form a ring,
R 7 and R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted oxy 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, and
M, ring A4, R 1 to R 6 , a to e, L 1 and L 2 , n1, and n2 are each independently the same as defined in Formula 3.

8. The organic electroluminescence device of claim 6 , wherein the organometallic compound represented by Formula 3 is represented by Formula 5:

and wherein, in Formula 5,
M, ring A4, R 1 to R 6 , a to e, L 2 , L 3 , n2, and n3 are each independently the same as defined in Formula 3.

9. The organic electroluminescence device of claim 6 , wherein the organometall

Assignees

• Samsung Display Co Ltd

Inventors

• HAN Junghoon
• Ko Soo-Byung
• Kim Sungbum
• Shin Sujin
• Ahn Eunsoo
• Lee Jaesung

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

• C09K2211/1048

  with oxygen · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title