Precursor for polyimide and use thereof

Patent metadata

Field	Value
Publication number	US-10626220-B2
Application number	US-201715825326-A
Country	US
Kind code	B2
Filing date	Nov 29, 2017
Priority date	Nov 30, 2016
Publication date	Apr 21, 2020
Grant date	Apr 21, 2020

Abstract

The present invention provides an amic acid ester oligomer having a structure of Formula (1) or (1′):

wherein G, P, R, R x , D, E and m are as defined in the specification. The present invention also provides a polyimide precursor composition comprising the amic acid ester oligomer, as well as a polyimide prepared from the composition.

First claim

What is claimed is:

1. An auric acid ester oligomer, having a structure of Formula (1) or (1′) below:

wherein
G is each independently a tetravalent organic group;
P is each independently a divalent organic group;
R is C 1 -C 14 alkyl, C 6 -C 14 aryl unsubstituted or substituted with one or more groups selected from hydroxyl and C 1 -C 4 alkyl, or a group having an ethylenically unsaturated bond;
R x is each independently H, C 1 -C 8 alkyl, or a group having an ethylenically unsaturated bond;
D is

a 5- or 6-membered heterocyclyl group containing nitrogen substituted with C 1 -C 8 alkyl, or C 1 -C 8 alkyl substituted with a 5- or 6-membered heterocyclyl group containing nitrogen;
wherein R 1 is H, methyl, trifluoromethyl, pentafluoroethyl,

—NHPh or —NHCH 3 ;
R 2 and R 3 are halo; R 4 is methyl or

and
E is

or —N(CH 3 ) 2 ; and
m is an integer from 1 to 100.

2. The oligomer according to claim 1 , wherein the group having an ethylenically unsaturated bond is selected from the group consisting of: ethenyl, propenyl, methylpropenyl, n-butenyl, iso-butenyl, ethenylphenyl, propenylphenyl, propenyloxymethyl, propenyloxyethyl, propenyloxypropyl, propenyloxybutyl, propenyloxypentyl, propenyloxyhexyl, methylpropenyloxymethyl, methylpropenyloxyethyl, methylpropenyloxypropyl, methylpropenyloxybutyl, methylpropenyloxypentyl, methylpropenyloxyhexyl, and a group of Formula (2):

wherein R 7 is phenylene, C 1 -C 8 alkylene, alkenylene, cycloalkylene, C 1 -C 8 hydroxyalkylene or

wherein n′ is an integer from 1 to 4, and R 8 is hydrogen or C 1 -C 4 alkyl.

3. The oligomer according to claim 1 , wherein R is each independently selected from the group consisting of:

4. The oligomer according to claim 1 , wherein the tetravalent organic group is selected from the group consisting of:

wherein X is each independently hydrogen, halo, C 1 -C 4 perfluoroalkyl, or C 1 -C 4 alkyl; and A and B at each occurrence are each independently a covalent bond, C 1 -C 4 alkylene unsubstituted or substituted with one or more groups selected from hydroxyl and C 1 -C 4 alkyl, C 1 -C 4 perfluoroalkylene, C 1 -C 4 alkyleneoxy, silylene, —O—, —S—, —C(O)—, —OC(O)—, —S(O) 2 —, —C(═O)O—(C 1 -C 4 alkylene)-OC(═O)—, —CONH—, phenyl, biphenylyl, or

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

5. The oligomer according to claim 1 , wherein the tetravalent organic group is selected from the group consisting of:

wherein Z is each independently hydrogen, methyl, trifluoromethyl or halo.

6. The oligomer according to claim 1 , wherein the divalent organic group is selected from the group consisting of:

wherein:
R 9 is each independently H, C 1 -C 4 alkyl, perfluoroalkyl, alkoxy, halo, —OH, —COOH, —NH 2 or —SH;
a is each independently an integer from 0 to 4;
b is each independently an integer from 0 to 4; and
R 10 is a covalent bond or a group selected from the group consisting of:

wherein
c and d are each independently an integer from 1 to 20;
R 9 and a are as defined above;
R 12 is —S(O) 2 —, —C(O)—, a covalent group, C 1 -C 4 alkyl or C 1 -C 4 perfluoroalkyl;
R 11 is each independently hydrogen, halo, phenyl, C 1 -C 4 alkyl, or C 1 -C 4 perfluoroalkyl; and
w and y are each an integer from 1 to 3.

7. The oligomer according to claim 6 , wherein the divalent organic group is selected from the group consisting of:

and a combination thereof,
wherein:
a is each independently an integer from 0 to 4; and
Z is each independently hydrogen, methyl, trifluoromethyl or halo.

8. The oligomer according to claim 1 , wherein the substituent D is:
(i)

wherein R 1 is H, methyl, trifluoromethyl, pentafluoroethyl,

—NHPh or —NHCH 3 ;
(ii)

wherein R 2 and R 3 are each independently —F or —Cl; and R 4 is methyl or

9. The oligomer according to claim 1 , wherein D is

10. The oligomer according to claim 1 , wherein m is an integer from 2 to 25.

11. A polyimide precursor composition, comprising an oligomer according to claim 1 and a solvent.

12. The composition according to claim 11 , wherein the solvent is selected from the group consisting of N-methylpyrrolidone, dimethylacetamide, dimethyl formamide, dimethyl sulfoxide, toluene, xylene, diethylene glycol dibutyl ether, N-octyl-2-pyrrolidone, N,N-dimethylcapramide, and a mixture thereof.

13. The composition according to claim 11 , wherein the polyimide precursor composition is a photosensitive polyimide precursor composition.

14. The composition according to claim 13 , further comprising a photobase generator, wherein the photobase generator is selected from the group consisting of:

and a combination thereof;
wherein R 17 is methyl or ethyl; R 15 is methyl, ethyl, propyl, phenyl, benzyl, —CH 2 CH 2 OH,

15. The compos

Assignees

• Eternal Mat Co Ltd

Inventors

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

Classifications

• C08G81/028

  containing polyamide sequences · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08G73/1067

  Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound · CPC title

• C08G73/1007 Primary

  from tetracarboxylic acids or derivatives and diamines · CPC title

• C08G69/44

  Polyester-amides · CPC title