Selenium-containing polyimide polymer, preparing method and use thereof

Patent metadata

Field	Value
Publication number	US-2019010290-A1
Application number	US-201615576890-A
Country	US
Kind code	A1
Filing date	Dec 16, 2016
Priority date	Oct 20, 2016
Publication date	Jan 10, 2019
Grant date	—

Abstract

The invention provides a selenium-containing polyimide polymer, preparation method and use thereof. The method comprises: (1) polymerizing a selenide diamine monomer with a dianhydride monomer to give a selenium-containing polyamic acid; and (2) performing thermal imidization on the selenium-containing polyamic acid obtained in the step (1) to give a selenium-containing polyimide polymer. In the invention, selenium is introduced into polyimides for increasing refractive index to 1.7 - 1.82 , this greatly improves the defects of low refractive index of the existing polyimide materials, thereby expanding its applications in the optics field.

First claim

1 . A selenium-containing polyimide polymer, having a general formula of:

wherein,
Ar is a selenide group;
R is selected from the group consisting of an aromatic ring, an aromatic ring derivative, an aliphatic ring and an aliphatic ring derivative; and
2≤n≤100.

2 . The selenium-containing polyimide polymer as claimed in claim 1 , wherein the selenide group has a general formula of: Ar 1 —Se—Ar 2 , Ai 3 -Se—Se—Ar 4 or Ar 5 —Se—Ar 6 —Se—Ar 7 —Se—Ar 8 , and Ar 1 to Ar 8 being independently selected from the group consisting of a phenyl group, a phenyl derivative, a naphthyl group, a naphthyl derivative and a C 2 -C 15 alkyl group.

3 . A method for preparing a selenium-containing polyimide polymer of claim 1 , comprising the steps of:
(1) polymerizing a selenide diamine monomer of formula (II) with a dianhydride monomer of formula (III) in an organic solvent to give a selenium-containing polyamic acid of formula (IV); and (2) performing thermal imidization on the selenium-containing polyamic acid of formula (IV) obtained in the step (1) to give a selenium-containing polyimide polymer of formula (V); the reaction scheme being as follows:

wherein 2≤n≤100;
R is selected from the group consisting of an aromatic ring, an aromatic ring derivative, an aliphatic ring and an aliphatic ring derivative; and
Ar is a selenide group.

4 . The method as claimed in claim 3 , wherein in the step (1), the polymerization temperature is 20-40° C.

5 . The method as claimed in claim 3 , wherein in the step (2), the temperature of thermal imidization is 60° C.-310° C.

6 . The method as claimed in claim 3 , wherein in the step (1), the selenide diamine monomer of formula (II) is 4, 4′-diamino diphenyl selenide, 4, 4′-diamino dinaphthyl selenide, 2, 2′-diamino dipropyl selenide, 6, 6′-diamino dihexyl selenide, 4, 4′-diamino diphenyl diselenide, 4, 4′-diamino dinaphthyl diselenide, 2, 2′-diamino dipropyl diselenide or 6, 6′-diamino dihexyl diselenide.

7 . The method as claimed in claim 3 , wherein in the step (2), the dianhydride monomer of formula (III) is pyromellitic dianhydride, 4,4′-oxydiphthalic anhydride, 4,4′-(hexafluoroisopropylidene)diphthalic anhydride, or cyclobutane tetracarboxylic dianhydride.

8 . The method as claimed in claim 6 , wherein the preparation method of 4,4′-diamino diphenyl selenide comprises the steps of:
reacting a para-aniline compound of (I) with selenium at 105-135° C. in an organic solvent; and
performing reduction on the resulting product after the reaction is complete, giving 4,4′-diamino diphenyl selenide,
the reaction scheme being as follows:

wherein X is I, Br or Cl.

9 . The method as claimed in claim 8 , wherein a molar ratio of the para-aniline compound to selenium is 9-11: 4-5.

10 . An optical material comprising the selenium-containing polyimide polymer of claim 1 , wherein the selenium-containing polyimide polymer has a refractive index of 1.7-1.82.

Assignees

• Univ Soochow

Inventors

• Zhu Jian
• Li Qilong
• Ding Chunlai
• Jiang Huinan
• Zhu Xiulin

Classifications

• C08G73/1071 Primary

  Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain · CPC title

• C08J2379/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C08G73/1057 Primary

  Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title