IP Library › Granted Patent US 12,477,942
Granted Patent B2
US 12,477,942 · App. 17/297,999 · Granted Nov 18, 2025

Organic metal compound and application thereof

Inventors: Liangliang Yan (Foshan, CN); Lei Dai (Foshan, CN); Lifei Cai (Foshan, CN)
Assignee: GUANGDONG AGLAIA OPTOELECTRONIC MATERIALS CO., LTD
H10K85/342C07F15/0033C09K11/06C09K2211/1033C09K2211/1037C09K2211/1048C09K2211/185H10K50/11H10K2101/10
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Quick Facts
Patent No.
US 12,477,942
App. No.
17/297,999
Granted
Nov 18, 2025
Kind
B2
Abstract

The present invention relates to an organic metal compound and application thereof. The organometallic compound has a structure as shown in Formula I. The compound provided by the present invention has the advantages of low sublimation temperature, high light and electricity stability, high luminous efficiency, long lifetime, high color saturation and the like, can be used in an organic light-emitting device, and particularly has a possibility of being applied to an AMOLED industry as a red luminescent phosphorescent material.

Claims (41)

1 . An organometallic compound, having a structural formula as shown in Formula I:

wherein:

one in A 1 to A 4 is a C—C bond connected with a ring E, one is a C-M bond connected with metal M, one is CR 4 , and another is CR 0 or N;

one in A 5 to A 8 is CR 3 , and the other three are independently represented as CR 0 or N;

M is a metal with the atomic weight greater than 40;

R 0 to R 4 are independently selected from hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C10 heteroalkyl group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, an amino group, a substituted or unsubstituted C1 to C10 silyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C8 heteroaryl group, a cyano group, a isocyano group, or a phosphino group, wherein the substitution refers to substitution by deuterium, F, Cl, Br, a C1 to C4 alkyl group, a C1 to C4 alkoxy group, a C3 to C6 cycloalkyl group, an amino group substituted by a C1 to C4 alkyl group, a cyano group, a isocyano group or a phosphino group;

at least one of R 3 and R 4 is not hydrogen;

Z is independently selected from O, S, Se, C(R) 2 , Si(R) 2 , NR, BR or POR, wherein R is independently selected from a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C 30 aryl group, a substituted or unsubstituted C1 to C18 heteroaryl group; and

X-Y is a monoanionic bidentate ligand, wherein the sum of a and b equals to a valence state of the metal M.

2 . The organometallic compound according to claim 1 , wherein:

X-Y is a OO type and CN type ligand; and

M is one of metals in Os, Ir, Pt, Pd, Ru, Rh or Au.

3 . The organometallic compound according to claim 2 , having a structure as shown in Formula II:

wherein:

n is a positive integer of 1 to 2;

A is CR 0 or N;

R 0 to R 4 are independently selected from hydrogen, deuterium, a substituted or unsubstituted C1 to C8 alkyl group, a substituted or unsubstituted C1 to C10 heteroalkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C8 aralkyl group, a substituted or unsubstituted C3 to C10 silyl group, or a C6 to C8 aryl group or C1 to C8 heteroaryl group unsubstituted or substituted by a C1 to C4 alkyl group; and

at least one of R 3 and R 4 is not hydrogen.

4 . The organometallic compound according to claim 3 , wherein A is CH.

5 . The organometallic compound according to claim 3 , wherein A is N.

6 . The organometallic compound according to claim 5 , wherein an R 3 substituent group is located adjacent to N.

7 . The organometallic compound according to claim 5 , wherein R 3 is D or an alkyl group with at most 4 carbon atoms.

8 . The organometallic compound according to claim 7 , wherein R 3 is an alkyl group at least containing one D.

9 . The organometallic compound according to claim 8 , wherein R 3 is CD3.

10 . The organometallic compound according to claim 3 , wherein the position of R 4 substituent group is a position adjacent to metal Ir—C bond.

11 . The organometallic compound according to claim 3 , wherein the position of R 4 substituent group is a position opposite to metal Ir—C bond.

12 . The organometallic compound according to claim 1 , wherein:

Z is O, S, NR or C(R) 2, and

R is independently selected from a substituted or unsubstituted C1 to C8 alkyl group.

13 . The organometallic compound according to claim 12 , wherein X—Y is different from a left ligand.

14 . The organometallic compound according to claim 13 , wherein X—Y is a 1,3-dione compound.

15 . An organic electroluminescence device, comprising the organometallic compound according to claim 1 .

16 . An organic electroluminescence device according to claim 15 , comprising a light-emitting layer, the light-emitting layer comprising a doped material of a phosphorescent host material, wherein the doped material is the organometallic compound according to claim 1 .

17 . The organometallic compound according to claim 3 , having one of the following compounds:

18 . The organometallic compound according to claim 17 , wherein:

Z is O, S or C(R) 2 , R 1 to R 4 are independently selected from hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C8 aralkyl group, or a C6 to C8 aryl group or C6 to C8 heteroaryl group unsubstituted or substituted by a C1 to C4 alkyl group; and

at least one of R 3 and R 4 is not hydrogen.

19 . The organometallic compound according to claim 18 , wherein:

R 1 to R 4 are independently selected from hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a phenyl group substituted by a C1 to C4 alkyl group; and

at least one of R 3 and R 4 is not hydrogen.

20 . The organometallic compound according to claim 19 , having one of the following structural formulas:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2021
From: YAN, LIANGLIANG; DAI, LEI; CAI, LIFEI
To: GUANGDONG AGLAIA OPTOELECTRONIC MATERIALS CO., LTD
Reel/Frame 056416/0913 →
Priority Claims (1)
CN 201811610359.5 · Dec 27, 2018 · national
Continuity (1)
Related Publication 20220115603A1 · Apr 14, 2022
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