Polyimide precursor composition and use thereof

Patent metadata

Field	Value
Publication number	US-10731004-B2
Application number	US-201715826871-A
Country	US
Kind code	B2
Filing date	Nov 30, 2017
Priority date	Nov 30, 2016
Publication date	Aug 4, 2020
Grant date	Aug 4, 2020

Abstract

The present invention provides a polyimide precursor composition comprising an amic acid ester oligomer of Formula (1):

and
a diamine of Formula (2) or (3):

wherein G, P, R, R x , P′, D, E and m are as defined herein.

The present invention also provides a dry film containing the polyimide precursor composition, as well as a polyimide film and polyimide laminate prepared from the composition.

First claim

What is claimed is:

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

a diamine of Formula (2) or (3):

wherein:
G is each independently a tetravalent organic group;
P is each independently a divalent organic group;
R is each independently 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, is each independently H, C 1 -C 8 alkyl, or an ethylenically unsaturated group;
P′ is each independently a divalent organic group;
D is each independently C 1 -C 8 alkyl unsubstituted or substituted with one or more groups selected from C 6 -C 14 aryl and a heterocyclyl group containing nitrogen; C 1 -C 8 haloalkyl; a heterocyclyl group containing oxygen unsubstituted or substituted with one or more groups selected from C 1 -C 8 alkyl, C 1 -C 8 hydroxyalkyl, oxo, and —NO 2 ; a heterocyclyl group containing nitrogen unsubstituted or substituted with one or more groups selected from oxo, C 1 -C 8 alkyl, and —NO 2 ;

R 1 is H; C 6 -C 14 aryl unsubstituted or substituted with one or more groups selected from C 1 -C 8 alkyl and C 1 -C 8 haloalkyl; a heterocyclyl group containing nitrogen; C 4 -C 10 cycloalkyl; C 1 -C 8 alkyl or C 1 -C 8 alkoxy unsubstituted or substituted with one or more groups selected from C 6 -C 14 aryl, a heterocyclyl group containing nitrogen, —S—R 4 ,

and —CN; C 1 -C 8 haloalkyl; C 1 -C 8 haloalkoxy; or —NR 5 R 6 ;
R 13 is

—OR 15 or C 1 -C 10 alkoxy;
R 2 , R 3 , R 4 , R 5 and R 6 may be the same or different and are each independently H; C 1 -C 8 alkyl or C 1 -C 8 alkoxy unsubstituted or substituted with one or more C 6 -C 14 aryl; C 6 -C 14 aryl or C 6 -C 14 aryloxy unsubstituted or substituted with one or more groups selected from C 1 -C 8 alkyl and —NO 2 ; halo; C 1 -C 8 haloalkyl; or a heterocyclyl group containing nitrogen;
R 14 is (meth)acryloyloxy;
R 15 is a C 4 -C 10 cycloalkyl or a heterocyclyl group containing oxygen;
t is an integer from 1 to 20;
E is each independently H; C 1 -C 14 alkyl; alkylamino; alkylthio; C 4 -C 10 cycloalkyl; a heterocyclyl group containing nitrogen or

with the provision that two E attached to the same carbon atom are not H at the same time;
or alternatively, two E attached to the same carbon atom form, together with the carbon atom, a C 6 -C 14 aryl group or a heterocyclyl group;
R 16 is each independently halo, hydroxyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkyl, or —NO 2 ;
i is an integer from 0 to 3;
j is an integer from 0 to 3; and
m is an integer from 1 to 100.

2. The composition 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):

where R 7 is phenylene, C 1 -C 8 alkylene, C 2 -C 8 alkenylene, C 3 -C 8 cycloalkylene, C 1 -C 8 hydroxyalkylene, or

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

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

4. The composition according to claim 1 , wherein the tetravalent organic group is each independently 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 composition according to claim 1 , wherein the divalent organic group is each independently selected from the group consisting of:

and the combination thereof;
wherein:
R 9 is each independently H, C 1 -C 4 alkyl, C 1 -C 4 perfluoroalkyl, C 1 -C 4 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.

6. The composition according to claim 1 , wherein the substituent D is:
(i) C 1 -C 8 alkyl unsubstituted or substituted with one or more groups selected from C 6 -C 4 aryl and a 5- or 6-membered heterocyclyl group containing nitrogen; C 1 -C 8 haloalkyl; a 5- or 6-membered heterocyclyl group containing oxygen unsubstituted or substituted with one or more groups selected from C 1 -C 8 alkyl and C 1 -C 8 hydroxyalkyl; or a 5- or 6-membered heterocyclyl group containing nitrogen substituted with one or more groups selected from C 1 -C 8 alkyl, oxo and —NO 2 ;

wherein R 1 is pyrrolyl, imidazolyl, pyrazolyl, pyrimidinyl, pyridinyl, H, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 6 -C 14 aryl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 6 -C 14 aryl-C 1 -C 8 alkoxy, —NH(C 6 -C 14 aryl), —NH(C 1 -C 8 alkyl), or the following groups:

wherein R 2 and R 3 are each independently H, C 1 -C 8 alkyl, C 6 -C 14 aryl, C 1 -C 8 alkyl substituted with one or more C 6 -C 14 aryl, or halo; and R 4 is H, C 1 -C 8 alkyl, C 6 -C 14 aryl, C 1 -C 8 alkyl substituted with one

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

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08G73/121 Primary

  Preparatory processes from unsaturated precursors and polyamines · CPC title

• C08G73/1032

  characterised by the solvent(s) used · CPC title

• C08G73/1025

  polymerised by radiations · CPC title

• H05K2203/1545

  Continuous processing, i.e. involving rolls moving a band-like or solid carrier along a continuous production path · CPC title