Anthracene-containing derivative, production process thereof and organic electroluminescent display device

Patent metadata

Field	Value
Publication number	US-10032988-B2
Application number	US-201414418244-A
Country	US
Kind code	B2
Filing date	May 27, 2014
Priority date	Dec 10, 2013
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

The invention discloses an anthracene-containing derivative, the production process thereof and an organic electroluminescent display device, wherein the anthracene-containing derivative has a general molecular structural formula of Formula I, wherein, R1 group is selected from an aromatic group or a fused aromatic group having a carbon atom number of 6 to 18, R2 group is selected from an amine group. By using the above described anthracene-containing derivative as a green phosphorescent host material, a green fluorescent host material, a hole injection material, or a hole transporting material in an organic electroluminescent display device, the light emitting efficiency and the light emitting brightness of the organic electroluminescent display device may be improved.

First claim

What is claimed is:

1. A production process of an anthracene-containing derivative, which is used as a green phosphorescent host material, a green fluorescent host material, a hole injection material or a hole transporting material in an organic electroluminescent display device, wherein the anthracene-containing derivative has a general molecular structural formula of:

wherein R 1 group is selected from an aromatic group or a fused aromatic group having a carbon atom number of 6 to 18, and R 2 group is selected from an amine group,
comprising the steps of:
under a protection gas atmosphere, adding a dibenzoanthracene bromide containing a R 1 group, an amine compound, sodium tert-butoxide, palladium acetate and a first organic solvent into a first reaction vessel, and continuously stirring the solution in the first reaction vessel;

wherein R 1 group is selected from an aromatic group or a fused aromatic group having a carbon atom number of 6 to 18;
adding tri-tert-butyl phosphine into the first reaction vessel dropwise, and heating to reflux.

2. The production process according to claim 1 , wherein the first organic solvent is toluene.

3. The production process according to claim 1 , wherein the dibenzoanthracene bromide containing R 1 group is produced by the steps of:
adding 1.2,5.6-di(2-bromo)benzo(9,10-dicarbonyl)anthracene and a second organic solvent into a second reaction vessel;
after 1.2,5.6-di(2-bromo)benzo(9,10-dicarbonyl)anthracene is dissolved into the second organic solvent, reducing the temperature of the second reaction vessel; adding butyl lithium into the second reaction vessel dropwise; after a second predetermined time, adding a solution of an iodide having a R 1 group into the second reaction vessel; raising the temperature of the second reaction vessel to normal temperature for reaction for a third predetermined time, so as to obtain an alcohol of a dibenzoanthracene bromide containing a R 1 group;
adding the alcohol of the dibenzoanthracene bromide containing a R 1 group, potassium iodide, sodium dihydrogen phosphate and a third organic solvent into a third reaction vessel;

heating to reflux for a fourth predetermined time, and then cooling to room temperature;
obtaining the dibenzoanthracene bromide containing a R 1 group.

4. The production process according to claim 3 , wherein the second organic solvent is tetrahydrofuran.

5. The production process according to claim 3 , wherein the third organic solvent is glacial acetic acid.

6. The production process according to claim 3 , wherein the 1.2,5.6-di(2-bromo)benzo(9,10-dicarbonyl)anthracene is produced by the steps of:
adding 7-bromonaphthofuran-1,3-dione and 2-iodonaphthalene into a fourth reaction vessel and heating the fourth reaction vessel;
adding aluminium trichloride into the fourth reaction vessel; performing reaction until no more hydrogen chloride is discharged; when the fourth reaction vessel is cooled, slowly pouring the solution in the fourth reaction vessel into an ice water solution of sodium hydroxide, so as to obtain (6-bromo-1-(6-bromo-2-naphthoyl)-2-naphthoyl)aluminum dichloride;
adding (6-bromo-1-(6-bromo-2-naphthoyl)-2-naphthoyl)aluminum dichloride and concentrated sulfuric acid into a fifth reaction vessel and heating the fifth reaction vessel.

7. The production process according to claim 1 , wherein R 2 group is selected from an aromatic amine group.

8. The production process according to claim 1 , wherein R 2 group is selected from an aromatic amine group having a carbon atom number of 6 to 30.

9. The production process according to claim 1 , wherein said R 1 group is phenyl, 9-phenanthryl, p-tolyl, 4-biphenyl, or 2-naphthyl.

10. The production process according to claim 1 , wherein said R 2 group is diphenylamino, N-phenyl-4-biphenylamino, di(4-biphenyl)amino, N-phenyl-2-naphthylamino, 2,2-dinaphthylamino, or N-phenyl-3,5-diphenyl phenylamino.

Assignees

• Boe Technology Group Co Ltd
• Jilin Oled Mat Tech Co Ltd

Inventors

• Li Na
• Ma Xiaoyu
• Wang Hui
• Huangfu Lujiang

Classifications

• C07C211/61

  with at least one of the condensed ring systems formed by three or more rings · CPC title

• C07C2603/26

  Phenanthrenes; Hydrogenated phenanthrenes · CPC title

• C07C46/00

  Preparation of quinones · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09B3/58

  Benzanthraquinones · CPC title