Polyimide precursor composition, use thereof and polyimide made therefrom

Patent metadata

Field	Value
Publication number	US-11034797-B2
Application number	US-201815941052-A
Country	US
Kind code	B2
Filing date	Mar 30, 2018
Priority date	Mar 31, 2017
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

The present disclosure relates to a polyimide precursor composition comprising an amic acid ester oligomer of formula (I):

wherein r, R x , G, P and R are as defined in the specification. Also, a use of the polyimide precursor composition and a polyimide made from the polyimide precursor composition.

First claim

What is claimed is:

1. A polyimide precursor composition, comprising an amic acid ester oligomer of formula (I):

wherein:
r is an integer ranging from 1 to 200;
Each R x is independently H, C 1 -C 14 alkyl or a moiety bearing an ethylenic-ally unsaturated group;
Each R is independently C 1 -C 14 alkyl, C 6 -C 14 aryl or aralkyl, or a moiety hearing an ethylenically unsaturated group;
Each G is independently a tetravalent organic group; and
Each F is independently a divalent organic group, wherein based on the total moles of the divalent organic groups P present in the composition, about 0.5 mol % to about 25 mol % of the divalent organic group P is a divalent organic group that is capable of forming a coordinate bond with a metal ion,
wherein the divalent organic group that is capable of forming a coordinate bond with a metal ion is selected from the group consisting of:

and
(vi) a combination of radicals (i)-(v),

wherein:
D is a bond, —NH—, —S—, —O—, phenylene or

E is 5 or 6-membered nitrogen-containing heterocyclyl

F is phenylene or

and
X is —NH—, —S— or —O—.

2. The polyimide precursor composition according to claim 1 , wherein r is an integer ranging from 5 to 150.

3. The polyimide precursor composition according to claim 1 , wherein the divalent organic group that is capable of forming a coordinate bond with a metal ion is selected from:

or a combination thereof wherein X is —NH—, —S— or —O—.

4. The polyimide precursor composition according to claim 1 , wherein based on the total moles of the divalent organic-groups P present in the composition, about 1 mol % to about 15 mol % of the divalent organic group P is an divalent organic group that is capable of forming a coordinate bond with a metal ion.

5. The polyimide precursor composition according to claim 1 , wherein tire remaining divalent organic groups P are each independently a divalent aromatic group or divalent heterocyclic-group other than tire radicals listed in (i) to (v) and are selected horn the group consisting of:

and a combination thereof,
wherein
each R 9 is independently H, C 1 -C 4 alkyl, C 1 -C 4 perfluoroalkyl, C 1 -C 4 alkoxyl or halogen;
each a is independently an integer from 0 to 4;
each b is independently an integer from 0 to 4;
R 10 is a covalent bond, or selected from the group consisting of:
—O—, —S—, —CH 2 —, —S(O) 2 —,

—C(CF 3 ) 2 —, —C(CH 3 ) 2 —,

wherein c and d are each independently an integer from 1 to 20, R 12 is —S(O) 2 —, a covalent bond, C 1 -C 4 alkylene or C 1 -C 4 perfluoroalkylene.

6. The polyimide precursor composition according to claim 1 , wherein G is selected from the group consisting of:

and a combination thereof,
wherein each X′ is independently H, halogen, C 1 -C 4 perfluoroalkyl, C 1 -C 4 alkyl; and A and B are independently, at each occurrence, a covalent bond, C 1 -C 4 alkylene unsubstituted or substituted with one or more radicals selected from C 1 -C 4 alkyl, C 1 -C 4 perfluoroalkylene, C 1 -C 4 alkoxylene, silylene, —O—, —S—, —C(O)—, —OC(O), —S(O) 2 —, —C(═O)O—(C 1 -C 4 alkylene)-OC(═O)—, phenylene, biphenylene or

wherein K is —O—, —S(O) 2 —, C 1 -C 4 alkylene or C 1 -C 4 perfluoroalkylene.

7. The polyimide precursor composition according to claim 1 , wherein each R is independently is selected from the group consisting of:

and a combination thereof.

8. The polyimide precursor composition according to claim 1 , farther comprising a cyclization promoter having the following formula:

wherein:
R 1 and R 2 are the same or different and are each independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, or C 1 -C 6 alkyl substituted with one or more C 6 -C 14 aryl,

R A is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 8 alkoxy unsubstituted or substituted with one or more C 6 -C 14 aryl, or —NR E R F ; R B , R C , R D , R E and R F are the same or different, and are each independently H, C 1 -C 14 alkyl unsubstituted or substituted with one or more C 6 -C 14 aryl, or C 6 -C 14 aryl;
R 3 , R 4 and R 5 are the same or different, and are each independently II, straight or branched C 1 -C 6 alkyl unsubstituted or substituted with one or more C 6 -C 14 aryl, straight or branched C 1 -C 6 hydroxyalkyl, straight or branched C 1 -C 6 cyanoalkyl, or C 6 -C 14 aryl; and
Y θ is an anionic group.

9. The polyimide precursor composition according to claim 1 , wherein the amic acid ester oligomer is in an amount of about 10 wt % to about 70 wt %, based on the total weight of the polyimide precursor composition.

10. The polyimide precursor composition according to claim 8 , herein the cyclization promoter is in an amount of about 0.1 parts by weight to about 2 parts by weight, based on 100 parts by weight of the amic acid ester oligomer of formula (I).

11. The polyimide precursor composition according to claim 1 , wherein the divalent organic group that is capable of forming a coordinate bond with a metal ion is selected horn:

or a combination thereof.

12. A polyimide prepared from the precursor composition according to claim 1 .

Assignees

• Eternal Mat Co Ltd

Inventors

• Chou Meng-Yen
• Wu Chung-Jen
• Ho Chang-Hong
• Chiang Shun-Jen
• Huang Po-Yu
• Cheng Chung-Kai

Classifications

• C08G73/0633

  with only two nitrogen atoms in the ring · CPC title

• C08G73/0273

  Polyamines containing heterocyclic moieties in the main chain · CPC title

• C08G73/16 Primary

  Polyester-imides · CPC title

• C08G73/1071 Primary

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

• C08G73/0605

  Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms · CPC title