IP Library Granted Patent US 11,034,797
Granted Patent B2
US 11,034,797 · App. 15/941,052 · Granted Jun 15, 2021

Polyimide precursor composition, use thereof and polyimide made therefrom

Inventors: Meng-Yen Chou (Kaohsiung, TW); Chung-Jen Wu (Kaohsiung, TW); Chang-Hong Ho (Kaohsiung, TW); Shun-Jen Chiang (Kaohsiung, TW); Po-Yu Huang (Kaohsiung, TW); Chung-Kai Cheng (Kaohsiung, TW)
Assignee: ETERNAL MATERIALS CO., LTD.
C08G73/1071C08G73/0273C08G73/0605C08G73/0627C08G73/0633C08G73/0644C08G73/1085C08G73/18
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Quick Facts
Patent No.
US 11,034,797
App. No.
15/941,052
Granted
Jun 15, 2021
Kind
B2
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.

Claims (47)

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 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2018
From: CHOU, MENG-YEN; WU, CHUNG-JEN; HO, CHANG-HONG; CHIANG, SHUN-JEN; HUANG, PO-YU; CHENG, CHUNG-KAI
To: ETERNAL MATERIALS CO., LTD.
Reel/Frame 045666/0233 →
Priority Claims (1)
TW 106111470 · Mar 31, 2017 · national
Continuity (1)
Related Publication 20180282482A1 · Oct 4, 2018