IP Library › Granted Patent US 12,545,697
Granted Patent B2
US 12,545,697 · App. 18/031,132 · Granted Feb 10, 2026

Metal complex and use thereof

Inventors: Shaofu Chen (Foshan, CN); Liangliang Yan (Foshan, CN); Lei Dai (Foshan, CN); Lifei Cai (Foshan, CN)
Assignee: SICHUAN AG-RAY NEW MATERIALS CO., LTD
C07F15/0086C09K11/06H10K50/17H10K59/875H10K85/00H10K85/342C09K2211/1033C09K2211/1037C09K2211/185H10K50/12
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,545,697
App. No.
18/031,132
Granted
Feb 10, 2026
Kind
B2
Abstract

The present disclosure relates to a metal complex and use thereof. The metal complex has a structure as shown in a formula (1). The metal complex provided by the present disclosure has advantages of good optical, electrical and thermal stability, high luminous efficiency, long service life, high color saturation and the like, can be used in an organic light-emitting device, particularly can be used as a green light-emitting phosphorescent material, and is possible to be used in the active-matrix organic light-emitting diode (AMOLED) industry.

Claims (49)

1 . A metal complex, having a structure as shown in a formula (1),

wherein at least one of R 1 -R 18 has a structure shown in a formula (2),

wherein

* represents a position of a linkage to the formula (1);

M is independently Pt or Pd;

X independently represents O, S, Se, and CRaRb;

L 1 -L 3 are each independently selected from a direct bonding single bond, O, S, Se, NRc, CRdRe, SO, SO 2 , and PO (Rf) (Rg);

L 4 is a single bond, O, substituted or unsubstituted C 1 -C 20 alkylene, substituted or unsubstituted C 3 -C 30 cycloalkylene, substituted or unsubstituted C 1 -C 20 heteroalkylene, substituted or unsubstituted C 7 -C 30 aralkylene, substituted or unsubstituted C 2 -C 20 alkenylene, substituted or unsubstituted C 3 -C 30 alkylidenesilyl, substituted or unsubstituted C 6 -C 30 arylene, substituted or unsubstituted C 3 -C 30 heteroarylene, substituted or unsubstituted C 3 -C 30 arylenesilyl, or substituted or unsubstituted C 0 -C 20 imino; and

the remaining R 1 -R 18 , R 101 -R 102 , and R a -R g are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 7 -C 30 aralkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 3 -C 30 alkylsilyl, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C 3 -C 30 heteroaryl, substituted or unsubstituted C 3 -C 30 arylsilyl, substituted or unsubstituted C 0 -C 20 amine, cyano, nitrile, isonitrile, or phosphino; or a ring structure formed by linking any two adjacent groups with each other; and the “substituted” refers to substitution with deuterium, halogen, C 1 -C 4 alkyl, or cyano; and

the substitution number of R 101 and R 102 independently represents a range from a non-substitution number to a maximum substitution number.

2 . The metal complex according to claim 1 , wherein the L 4 is a single bond, O, and one of the following structures:

wherein

* represents a position of a linkage of the formula (1) and the formula (2);

the number of R x represents a range from a non-substitution number to a maximum substitution number, and when the R x is polysubstituted, adjacent two substituents may be linked to each other to form a ring structure; and

the R x and R y are independently selected from hydrogen, deuterium, halogen, C 1 -C 4 alkyl, or cyano.

3 . The metal complex according to claim 2 , wherein the R 1 , the R 2 , the R 7 , the R 8 , the R 10 , the R 11 , the R 18 , the R 101 , the R 102 , the R a and the R b are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C 1 -C 8 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 1 -C 8 heteroalkyl, substituted or unsubstituted C 7 -C 10 aralkyl, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 3 -C 8 alkylsilyl, substituted or unsubstituted C 6 -C 10 aryl, substituted or unsubstituted C 3 -C 10 heteroaryl, substituted or unsubstituted C 3 -C 10 arylsilyl, substituted or unsubstituted C 0 -C 6 amido, or cyano.

4 . The metal complex according to claim 3 , wherein the R 1 , the R 2 , the R 7 , the R 8 , the R 10 , the R 11 , the R 18 , the R 101 , the R 102 , the R a and the R b are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C 1 -C 8 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 1 -C 8 heteroalkyl, substituted or unsubstituted C 7 -C 10 phenylalkyl, substituted or unsubstituted C 6 -C 10 aryl, or substituted or unsubstituted C 3 -C 10 heteroaryl;

the R x and the R y are independently selected from hydrogen, deuterium, halogen, or C 1 -C 4 alkyl.

5 . The metal complex according to claim 4 , wherein the R 18 is deuterium, substituted or unsubstituted straight-chain carbon atom C 1 -C 4 alkyl, or substituted or unsubstituted C 3 -C 6 cycloalkyl, and the “substituted” refers to substitution with deuterium or halogen.

6 . An electroluminescent device, comprising a cathode, an anode, and an organic layer arranged between the cathode and the anode, wherein at least one of the organic layer comprises the metal complex according to claim 5 .

7 . An electroluminescent device, comprising a cathode, an anode, and an organic layer arranged between the cathode and the anode, wherein at least one of the organic layer comprises the metal complex according to claim 4 .

8 . The metal complex according to claim 4 , wherein at least one of the R 1 and the R 2 is not hydrogen.

9 . An electroluminescent device, comprising a cathode, an anode, and an organic layer arranged between the cathode and the anode, wherein at least one of the organic layer comprises the metal complex according to claim 8 .

10 . An electroluminescent device, comprising a cathode, an anode, and an organic layer arranged between the cathode and the anode, wherein at least one of the organic layer comprises the metal complex according to claim 3 .

11 . An electroluminescent device, comprising a cathode, an anode, and an organic layer arranged between the cathode and the anode, wherein at least one of the organic layer comprises the metal complex according to claim 2 .

12 . The metal complex according to claim 1 , having a structure as shown in a formula (3),

wherein at least one of R 1 -R 18 has a structure shown in a formula (2),

wherein the *, the X, the L 4 , the R 1 -R 18 , the R 101 -R 102 , and R a -R b are as defined above.

13 . The metal complex according to claim 12 , having a structure as shown in a formula (4),

wherein

the X independently represents O, S, Se, and CRaRb;

the L 4 is a single bond, O, substituted or unsubstituted C 1 -C 10 alkylene, substituted or unsubstituted C 3 -C 10 cycloalkylene, substituted or unsubstituted C 2 -C 10 heteroalkylene, substituted or unsubstituted C 7 -C 20 aralkylene, substituted or unsubstituted C 2 -C 20 alkenylene, substituted or unsubstituted C 3 -C 30 alkylidenesilyl, substituted or unsubstituted C 6 -C 30 arylene, substituted or unsubstituted C 3 -C 30 heteroarylene, substituted or unsubstituted C 3 -C 30 arylenesilyl, or substituted or unsubstituted C 0 -C 20 imino; and

R 1 , R 2 , R 7 , R 8 , R 10 , R 11 , R 18 , the R 101 , the R 102 , R a , and R b are as defined above.

14 . An electroluminescent device, comprising a cathode, an anode, and an organic layer arranged between the cathode and the anode, wherein at least one of the organic layer comprises the metal complex according to claim 13 .

15 . An electroluminescent device, comprising a cathode, an anode, and an organic layer arranged between the cathode and the anode, wherein at least one of the organic layer comprises the metal complex according to claim 12 .

16 . An electroluminescent device, comprising a cathode, an anode, and an organic layer arranged between the cathode and the anode, wherein at least one of the organic layer comprises the metal complex according to claim 1 .

17 . The electroluminescent device according to claim 16 , wherein the organic layer comprises a light-emitting layer, and the metal complex is used as a green light-emitting material in the light-emitting layer; or

the organic layer comprises a hole injection layer, and the metal complex is used as a hole injection material in the hole injection layer.

18 . A metal complex, having one of the following structural formulas,

19 . An electroluminescent device, comprising a cathode, an anode, and an organic layer arranged between the cathode and the anode, wherein at least one of the organic layer comprises the metal complex according to claim 18 .

20 . A precursor of the metal complex, having a structure as shown in a formula (5),

wherein at least one of the R 1 -R 18 has a structure shown in the formula (2),

wherein

* represents a position of a linkage to the formula (5);

X independently represents O, S, Se, and CRaRb;

L 1 -L 3 are each independently selected from a direct bonding single bond, O, S, Se, NRc, CRdRe, SO, SO 2 , and PO (Rf) (R g );

L 4 is a single bond, O, substituted or unsubstituted C 1 -C 20 alkylene, substituted or unsubstituted C 3 -C 30 cycloalkylene, substituted or unsubstituted C 1 -C 20 heteroalkylene, substituted or unsubstituted C 7 -C 30 aralkylene, substituted or unsubstituted C 2 -C 20 alkenylene, substituted or unsubstituted C 3 -C 30 alkylidenesilyl, substituted or unsubstituted C 6 -C 30 arylene, substituted or unsubstituted C 3 -C 30 heteroarylene, substituted or unsubstituted C 3 -C 30 arylenesilyl, or substituted or unsubstituted C 0 -C 20 imino; and

the remaining R 1 -R 18 , R 101 -R 102 , and R a -R g are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 1 -C 20 heteroalkyl, substituted or unsubstituted C 7 -C 30 aralkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 3 -C 30 alkylsilyl, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C 3 -C 30 heteroaryl, substituted or unsubstituted C 3 -C 30 arylsilyl, substituted or unsubstituted C 0 -C 20 amine, cyano, nitrile, isonitrile, or phosphino; or a ring structure formed by linking any two adjacent groups with each other; and the “substituted” refers to substitution with deuterium, halogen, C 1 -C 4 alkyl, or cyano; and

the substitution number of R 101 and R 102 independently represents a range from a non-substitution number to a maximum substitution number.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 12, 2023
From: CHEN, SHAOFU; YAN, LIANGLIANG; DAI, LEI; CAI, LIFEI
To: SICHUAN AG-RAY NEW MATERIALS CO., LTD
Reel/Frame 063307/0552 →
Priority Claims (1)
CN 202011178409.4 · Oct 29, 2020 · national
Continuity (1)
Related Publication 20230389408A1 · Nov 30, 2023
References Cited (18)
US 8772485B2 · Che et al. · 2014 [cited by applicant]
US 8877353B2 · Che · 2014 [cited by examiner]
US 9783564B2 · Kottas · 2017 [cited by examiner]
US 11011711B2 · Kim · 2021 [cited by examiner]
US 20060134461A1 · Huo · 2006 [cited by examiner]
US 20120018711A1 · Che · 2012 [cited by examiner]
US 20180062088A1 · Cho · 2018 [cited by examiner]
US 20180141969A1 · Hwang et al. · 2018 [cited by applicant]
US 20180233679A1 · Baik et al. · 2018 [cited by applicant]
US 20210332290A1 · Peng et al. · 2021 [cited by applicant]
CN 103097395A · 2013 [cited by applicant]
CN 104245713A · 2014 [cited by applicant]
CN 107056844A · 2017 [cited by applicant]
CN 110872325A · 2020 [cited by applicant]
WO WO2005042444A2 · 2005 [cited by examiner]
WO WO2012009957A1 · 2012 [cited by examiner]
WO WO2019128895A1 · 2019 [cited by examiner]
WO WO2020134569A1 · 2020 [cited by examiner]