IP Library › Granted Patent US 12,703,715
Granted Patent B2
US 12,703,715 · App. 18/030,964 · Granted Aug 11, 2026

Organometallic compound and application thereof

Inventors: Liangliang Yan (Foshan, CN); Lei Dai (Foshan, CN); Lifei Cai (Foshan, CN)
Assignee: GUANGDONG AGLAIA OPTOELECTRONIC MATERIALS CO., LTD
C07F15/0033H10K50/12H10K85/00H10K85/342
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Quick Facts
Patent No.
US 12,703,715
App. No.
18/030,964
Granted
Aug 11, 2026
Kind
B2
Abstract

The present disclosure relates to an organometallic compound and application thereof. The organometallic compound has a structure as shown in a formula (1). The compound provided by the present disclosure has the advantages of high optical and electrochemical stability, small half-peak width of emission spectrum, high color saturation, high luminous efficiency and long device service life, and can be used in organic electroluminescent devices. In particular, the compound has the potential for application in the AMOLED industry as a green light-emitting dopant.

Claims (36)

1 . An organometallic compound, having a structure formula as shown in the following formula (1):

wherein

m is 1, 2, or 3, and when m is 1, the two L2 are the same or different;

the number of Ra, Rb and Rc is from 1 to a maximum substitution number;

Ra, Rb, Rc, Rd and Re are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 20 cycloalkyl, substituted or unsubstituted C 6 -C 18 aryl, substituted or unsubstituted tri-C 1 -C 10 alkyl silyl, substituted or unsubstituted tri-C 6 -C 12 aryl silyl, and substituted or unsubstituted di-C 1 -C 10 alkyl mono-C 6 -C 30 aryl silyl;

R 1 -R 8 are independently selected from hydrogen, deuterium, halogen, hydroxyl, sulfhydryl, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 1 -C 10 heteroalkyl, substituted or unsubstituted C 3 -C 20 cycloalkyl, substituted or unsubstituted C 2 -C 10 alkenyl, substituted or unsubstituted C 2 -C 10 alkynyl, substituted or unsubstituted C 6 -C 18 aryl, substituted or unsubstituted C 2 -C 17 heteroaryl, substituted or unsubstituted tri-C 1 -C 10 alkyl silyl, substituted or unsubstituted tri-C 6 -C 12 aryl silyl, and substituted or unsubstituted di-C 1 -C 10 alkyl mono-C 6 -C 30 aryl silyl, or two adjacent groups of R 1 -R 8 may be connected with each other to form an aliphatic ring structure or an aromatic ring structure;

the heteroalkyl and the heteroaryl at least contain one O, N or S heteroatom;

and the “substituted” refers to substitution with deuterium, F, Cl, Br, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, amino substituted with C 1 -C 6 alkyl, nitrile, isonitrile, or phosphino, and the substitution ranges from a single substitution number to a maximum substitution number.

2 . The organometallic compound according to claim 1 , wherein when the m is 1 or 2, the two L1 or the two L2 are the same.

3 . The organometallic compound according to claim 2 , wherein the Ra, the Rd and the Re are hydrogen.

4 . The organometallic compound according to claim 3 , wherein at least one of the R 1 -R 4 is not hydrogen.

5 . The organometallic compound according to claim 3 , wherein at least one of the R 5 -R 8 is not hydrogen.

6 . The organometallic compound according to claim 3 , wherein at least one of the R 1 -R 4 is not hydrogen, and at least one of the R 5 -R 8 is not hydrogen.

7 . The organometallic compound according to claim 6 , wherein one of the R 1 -R 4 is deuterium, C 1 -C 5 alkyl substituted or unsubstituted with deuterium, or C 3 -C 5 cycloalkyl substituted or unsubstituted with deuterium, one of the R 5 -R 8 is deuterium, C 1 -C 5 alkyl substituted or unsubstituted with deuterium, or C 3 -C 5 cycloalkyl substituted or unsubstituted with deuterium, and the other of R 1 -R 8 are hydrogen.

8 . The organometallic compound according to claim 6 , wherein the R 5 and the R 6 , the R 6 and the R 7 , or the R 7 and the R 8 are connected with each other to form a parallel ring structure as shown in a formula (2):

wherein * indicates a connecting position;

Y 1 -Y 4 are independently CR 0 or N;

Z 1 is selected from O or S;

R 0 is independently hydrogen, deuterium, F, cyano, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 20 cycloalkyl, substituted or unsubstituted C 2 -C 30 alkenyl, substituted or unsubstituted C 2 -C 30 alkynyl, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C 1 -C 30 heteroaryl, substituted or unsubstituted tri-C 1 -C 10 alkyl silyl, substituted or unsubstituted tri-C 6 -C 30 aryl silyl, or substituted or unsubstituted di-C 1 -C 10 alkyl mono-C 6 -C 30 aryl silyl;

and the “substituted” refers to substitution with deuterium, F, Cl, Br, C 1 -C 4 alkyl, C 1 -C 4 alkoxyl, C 3 -C 6 cycloalkyl, amino substituted with C 1 -C 4 alkyl, nitrile, isonitrile, or phosphino.

9 . The organometallic compound according to claim 6 , wherein the R 4 and the R 5 are connected with each other to form an aliphatic ring structure as shown in a formula (3):

wherein * indicates a connecting position;

Z 2 and Z 3 are independently selected from O, S, N (R 0 ) and C(R 0 ) 2 , and at least one of the Z 2 and Z 3 is C(R 0 ) 2 ;

R 0 is independently hydrogen, deuterium, F, cyano, substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 3 -C 20 cycloalkyl, substituted or unsubstituted C 2 -C 30 alkenyl, substituted or unsubstituted C 2 -C 30 alkynyl, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C 1 -C 30 heteroaryl, substituted or unsubstituted tri-C 1 -C 10 alkyl silyl, substituted or unsubstituted tri-C 6 -C 30 aryl silyl, or substituted or unsubstituted di-C 1 -C 10 alkyl mono-C 6 -C 30 aryl silyl;

and the “substituted” refers to substitution with deuterium, F, Cl, Br, C 1 -C 4 alkyl, C 1 -C 4 alkoxyl, C 3 -C 6 cycloalkyl, amino substituted with C 1 -C 4 alkyl, nitrile, isonitrile, or phosphino.

10 . The organometallic compound according to claim 1 , wherein at least one of the Rb and the Rc is not hydrogen.

11 . The organometallic compound according to claim 10 , wherein at least one of the Rb and the Rc is substituted or unsubstituted C 1 -C 6 alkyl, or substituted or unsubstituted C 3 -C 6 cycloalkyl.

12 . The organometallic compound according to claim 11 , wherein at least one of the Rb and the Rc is substituted or unsubstituted C 1 -C 6 alkyl, or substituted or unsubstituted C 3 -C 6 cycloalkyl, and the other group is hydrogen.

13 . The organometallic compound according to claim 3 , wherein the L1 has one of the following structural formulas, or is partially or completely deuterated or fluorinated correspondingly,

14 . The organometallic compound according to claim 3 , wherein the L2 preferably has one of the following structural formulas, or is partially or completely deuterated or fluorinated correspondingly,

15 . The organometallic compound according to claim 1 , wherein the compound as shown in the formula (1) has one of the following structural formulas, or is partially or completely deuterated or fluorinated correspondingly,

16 . The organometallic compound according to claim 1 in an organic electroluminescent device.

17 . The organometallic compound according to claim 16 , wherein the organometallic compound is used as a green light-emitting doping material of a light-emitting layer in the organic electroluminescent device.

18 . The organometallic compound according to claim 3 , wherein at least one of the Rb and the Rc is not hydrogen.

19 . The organometallic compound according to claim 2 in an organic electroluminescent device.

20 . The organometallic compound according to claim 3 in an organic electroluminescent device.