Platinum complex having ONCN tetradentate ligand and containing carbazole

Patent metadata

Field	Value
Publication number	US-12540153-B2
Application number	US-202118038680-A
Country	US
Kind code	B2
Filing date	Oct 24, 2021
Priority date	Nov 30, 2020
Publication date	Feb 3, 2026
Grant date	Feb 3, 2026

Abstract

The present invention relates to a platinum complex having an ONCN tetradentate ligand and containing carbazole, and the platinum complex has a structure as shown in a formula (I). The complex has bright green light emission wavelengths, and can be used in the field of OLED organic electroluminescent materials. By means of the structural design, the present invention can improve the heavy atomic effect of phosphorescent materials, enhance spin-spin coupling, and achieve high-efficiency conversion of T1-S0, thereby achieving high luminous efficiency. Moreover, a platinum complex molecule having an ONCN tetradentate ligand has simple synthetic steps and may modifiable sites. The steric hindrance added by the carbazole group contained can effectively reduce the aggregation effect between molecules, avoid the formation of an exciplex, and further improve the color purity and the luminous efficiency.

First claim

The invention claimed is:

1 . A platinum complex having an ONCN tetradentate ligand and containing carbazole, having a structure as shown in a formula (I):

wherein R 1 -R 24 are independently selected from hydrogen, deuterium, sulfur, halogen, hydroxyl, acyl, alkoxyl containing 1-30 C atoms, acyloxyl, amino, nitro, acylamino, cyano, carboxyl, styrenyl, aminoformyl, benzylcarbonyl, aryloxyl, diarylamino, saturated alkyl containing 1-30 C atoms, substituted or unsubstituted aryl containing 6-30 C atoms, and substituted or unsubstituted heteroaryl containing 5-30 C atoms, or adjacent groups of the R 1 -R 24 are connected to each other through a covalent bond to form a ring;
Ar is selected from substituted or unsubstituted aryl containing 6-30 carbon atoms, and substituted or unsubstituted heteroaryl containing 3-30 carbon atoms;
and the “substituted” refers to substitution with deuterium, halogen, amino, nitro, cyano, or C 1 -C 4 alkyl.

2 . The platinum complex according to claim 1 , wherein the R 1 -R 24 are independently selected from hydrogen, deuterium, sulfur, halogen, alkoxyl containing 1-10 C atoms, cyano, styrenyl, aryloxyl, diarylamino, saturated alkyl containing 1-10 C atoms, substituted or unsubstituted aryl containing 6-20 C atoms, and substituted or unsubstituted heteroaryl containing 5-20 C atoms, or adjacent groups of the R 1 -R 24 are connected to each other through a covalent bond to form a ring.

3 . The platinum complex according to claim 2 , wherein the Ar is selected from substituted or unsubstituted 2,3- or 3,4-benzoaryl containing 6-30 carbon atoms, substituted or unsubstituted 2,3- or 3,4-benzoheteroaryl containing 3-30 carbon atoms, substituted or unsubstituted phenylaryl containing 6-20 carbon atoms, and substituted or unsubstituted phenylheteroaryl containing 6-20 carbon atoms.

4 . A platinum complex having an ONCN tetradentate ligand and containing, having a structure as shown in a formula (II) or (III):

wherein R 1 -R 24 are independently selected from hydrogen, deuterium, halogen, cyano, aryloxyl, diarylamino, saturated alkyl containing 1-4 C atoms, substituted or unsubstituted aryl containing 6-10 C atoms, and substituted or unsubstituted heteroaryl containing 5-10 C atoms, or adjacent groups of the R 1 -R 24 are connected to each other through a covalent bond to form a ring;
and A and B are substituted or unsubstituted aryl containing 6-30 C atoms, or substituted or unsubstituted heteroaryl containing 5-30 C atoms.

5 . The platinum complex according to claim 4 , wherein among the R 1 -R 24 , R 17 and R 19 are tert-butyl, and the other groups are hydrogen.

6 . The platinum complex according to claim 5 , wherein the A and the B are a substituted or unsubstituted five-membered heteraromatic ring, a six-membered aromatic ring, a six-membered heteraromatic ring, or a five-membered benzo-heteraromatic ring.

7 . A platinum complex having an ONCN tetradentate ligand and containing carbazole, having a structure as shown in one of the following formulas:

8 . A precursor of the platinum complex according to claim 1 , having the following structural formula:

wherein R 1 -R 24 and Ar are defined the same as above.

9 . A preparation method of the platinum complex according to claim 1 , comprising a preparation route of: subjecting A R to a coupling reaction with B R to obtain C R ; subjecting the C R to a demethylation reaction under acidic conditions to obtain D R ; subjecting the D R to a hydroxyl halogenation reaction to obtain E R ; subjecting the E R to a coupling reaction with F R to obtain G R ;

then subjecting the G R to a coupling reaction with a halogenated aromatic derivative to obtain H R ; subjecting the H R to demethylation under acidic conditions to obtain I R ; and finally, subjecting the I R to an ONCN tetradentate coordination reaction with metal platinum to obtain a J R type luminescent material,

10 . A precursor of the platinum complex according to claim 2 , having the following structural formula:

wherein R 1 -R 24 and Ar are defined the same as above.

11 . A precursor of the platinum complex according to claim 3 , having the following structural formula:

wherein R 1 -R 24 and Ar are defined the same as above.

12 . An OLED comprising a light-emitting layer, wherein the light-emitting layer comprises a phosphorescent dopant material, and the phosphorescent dopant material comprises the platinum complex as claimed in claim 1 .

13 . An OLED comprising a light-emitting layer, wherein the light-emitting layer comprises a phosphorescent dopant material, and the phosphorescent dopant material comprises the platinum complex as claimed in claim 2 .

14 . An OLED comprising a light-emitting layer, wherein the light-emitting layer comprises a phosphorescent dopant material, and the phosphorescent dopant material comprises the platinum complex as claimed in claim 3 .

15 . An OLED comprising a light-emitting layer, wherein the light-emitting layer comprises a phosphorescent dopant material, and the phosphorescent dopant material comprises the platinum complex as claimed in claim 4 .

16 . An OLED comprising a light-emitting layer, wherein the light-emitting layer comprises a phosphorescent dopant material, and the phosphorescent dopant material comprises the platinum complex as claimed in claim 5 .

17 . An OLED comprising a light-emitting layer, wherein the light-emitting layer comprises a phosphorescent dopant material,

Assignees

• Guangdong Aglaia Optoelectronic Mat Co Ltd

Inventors

• Wu Xinwei
• Li Huiyang
• Dai Lei
• Cai Lifei

Classifications

• H10K50/12

  comprising dopants · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• H10K85/346

  comprising platinum · CPC title

• H10K85/00

  Organic materials used in the body or electrodes of devices covered by this subclass · CPC title