Thermally activated delayed fluorescent deep-red light polymer material and method of fabricating same

Patent metadata

Field	Value
Publication number	US-11512245-B2
Application number	US-201916319781-A
Country	US
Kind code	B2
Filing date	Jan 16, 2019
Priority date	Nov 14, 2018
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

A thermally activated delayed fluorescent (TADF) deep-red light polymer material is provided, and includes a main chain to polymerize a TADF molecular structure, and a side chain to connect with an alkyl chain. The TADF polymer material of this structure has excellent TADF characteristics and solubility. Further, the material can be used to fabricate an electroluminescent device by a solution processing, and a good device effect can be obtained.

First claim

The invention claimed is:

1. A thermally activated delayed fluorescent deep-red light polymer material having repeating units as follows:

2. The thermally activated delayed fluorescent deep-red light polymer material according to claim 1 , wherein the thermally activated delayed fluorescent deep-red light polymer material is synthesized from a monomer compound A and a monomer compound B, and wherein:
a structural formula of the monomer compound A is:

and
a structural formula of the monomer compound B is:

3. The thermally activated delayed fluorescent deep-red light polymer material according to claim 2 , wherein the thermally activated delayed fluorescent deep-red light polymer material is synthesized from the monomer compound A and the monomer compound B through a synthesizing route as follows:

4. The thermally activated delayed fluorescent deep-red light polymer material according to claim 2 , wherein the monomer compound A is synthesized through a synthesizing route as follows:

5. The thermally activated delayed fluorescent deep-red light polymer material according to claim 2 , wherein the monomer compound B is synthesized through a synthesizing route as follows:

6. A method of fabricating a thermally activated delayed fluorescent deep-red light polymer material according to claim 1 , comprising following steps of:
adding a monomer compound A, a monomer compound B, palladium acetate and tri-tert-butylphosphine tetrafluoroborate into a reaction flask, so as to obtain a mixture;
adding NaOt-Bu and toluene into the reaction flask in a glove box, reacting at 100-120° C. for 40-60 hours, and cooling to room temperature, so as to obtain a reaction product;
precipitating the reaction product by using a mixed solvent of methanol and acetone, so as to obtain a polymer product; and
placing the polymer product in n-hexane and acetone for extraction, and then drying the polymer product to obtain the thermally activated delayed fluorescent deep red light polymer material, wherein:
a structural formula of the monomer compound A is:

and
a structural formula of the monomer compound B is:

7. The method of fabricating the thermally activated delayed fluorescent deep-red light polymer material according to claim 6 , wherein a molar mass ratio of the monomer compound A, the monomer compound B, palladium acetate and tri-tert-butylphosphine tetrafluoroborate is: (4-6):(4-6):(1.5-2.5):(5-7).

8. The method of fabricating the thermally activated delayed fluorescent deep-red light polymer material according to claim 6 , wherein the monomer compound A is synthesized by steps of:
adding 1-iodo-3-fluoro-4-bromo-benzonitrile and copper powder into a reaction flask in an argon atmosphere, introducing deoxygenated toluene into the reaction flask after pumping, then reacting at 100 to 120° C. for 20 to 30 hours, and cooling to room temperature, so as to obtain a reaction solution; and
pouring the reaction solution into an ice water, filtering the reaction solution to obtain a solid, dissolving the solid in dichloromethane followed by spinning to form a gel product, and separating and purifying the gel product by column chromatography to obtain the monomer compound A.

9. The method of fabricating the thermally activated delayed fluorescent deep-red light polymer material according to claim 6 , wherein the monomer compound B is synthesized by steps of:
adding 3,3′-dihexyl-1,1′-dihydroxydiphenylamine, potassium hydroxide and a catalyst into a reaction flask, introducing carbon tetrachloride into the reaction flask after pumping, reacting at 100 to 120° C. for 20 to 30 hours, and cooling to room temperature, so as to obtain a reaction solution; and
pouring the reaction solution into an ice water, extracting with dichloromethane, combining organic phases, followed by spinning to form a gel product, and separating and purifying the gel product by column chromatography to obtain the monomer compound B.

10. An organic electroluminescent device, comprising a light-emitting layer, wherein the light-emitting layer comprises the thermally activated delayed fluorescent deep-red light polymer material according to one of claim 1 .

Assignees

• Wuhan China Star Optoelectronics Semiconductor Display Tech Co Ltd

Inventors

• Luo Jiajia
• Li Xianjie

Classifications

• C08G73/0688 Primary

  with only one nitrogen atom in the ring, e.g. polyquinolines · CPC title

• C08G18/773

  halogens · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1022

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title