Polyimides

Patent metadata

Field	Value
Publication number	US-10793676-B2
Application number	US-201716084348-A
Country	US
Kind code	B2
Filing date	Oct 26, 2017
Priority date	Nov 3, 2016
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

Abstract

A polyimide polymer that includes the reaction product of: (a) at least one diamine selected from the group consisting of a diamine of Structure (I)

(b) at least one tetracarboxylic acid dianhydride, and optionally (c) at least one compound containing a first functional group reactive with an amine or an anhydride and at least one second functional group selected from the group consisting of an unsubstituted alkenyl group and an unsubstituted alkynyl group. Each variable in the above formula is defined in the specification.

First claim

What is claimed is:

1. A polyimide polymer containing the reaction product of components (a), (b), and optionally (c), wherein components (a), (b), and (c) are:
(a) at least one diamine of Structure (I):

(b) at least one tetracarboxylic acid dianhydride, and optionally;
(c) at least one compound containing a first functional group reactive with an amine or an anhydride and at least one second functional group selected from the group consisting of an unsubstituted alkenyl group and an unsubstituted alkynyl group, wherein the first functional group reactive to an amine is selected from the group consisting of an anhydride group, an acid halide group, an epoxy group, and an isocyanate group and the first functional group reactive to an anhydride is selected from the group consisting of an amino group, a hydroxyl group, and a thiol group,
wherein each of R 6 , R 7 , R 8 , R 9 , and R 10 , independently, is H, an unsubstituted C 1 -C 6 linear or branched alkyl group, or an unsubstituted C 5 -C 8 cycloalkyl group; each R 11 , independently, is H, an unsubstituted C 1 -C 6 linear or branched alkyl group, or an unsubstituted C 5 -C 8 cycloalkyl group; each R 12 , independently, is H, an unsubstituted C 1 -C 6 linear or branched alkyl group, or an unsubstituted C 5 -C 8 cycloalkyl group; x is an integer from 0 to 3; y is an integer from 0 to 2; and each z, independently, is an integer from 1 to 4.

2. The polymer of claim 1 , wherein the —O—(CH 2 ) z —CH═CH 2 group on the indane moiety is at the para position relative to the group —C(R 9 R 10 )— and the other —O—(CH 2 ) z —CH═CH 2 group is at the para position relative to the indane moiety.

3. The polymer of claim 1 , wherein the —NH 2 group on the indane moiety is at the ortho position relative to the —O—(CH 2 ) z —CH═CH 2 group on the indane moiety and the —NH 2 group on the phenyl moiety is at the ortho position relative to the —O—(CH 2 ) z —CH═CH 2 group on the phenyl moiety.

4. The polymer of claim 1 , wherein each of R 6 , R 9 , and R 10 is an unsubstituted C 1 -C 6 linear or branched alkyl group.

5. The polymer of claim 4 , wherein each of R 6 , R 9 , and R 10 is CH 3 , CH 2 CH 3 , or CH(CH 3 ) 2 .

6. The polymer of claim 1 , wherein x is 0 or 1, y is 0 or 1, R 7 is H, and R 8 is H.

7. The polymer of claim 1 , wherein the diamine of Structure (I) is selected from the group consisting of:

8. The polymer of claim 1 , wherein the tetracarboxylic acid dianhydride is selected from the group consisting of:

9. The polymer of claim 1 , wherein the molar ratio of components (a) and (b) to component (c) ranges from 1.01 and 1.4.

10. The polymer of claim 1 , wherein the molar ratio of components (a and (b to component (c) ranges from 0.8 and 0.99.

11. A polyamic acid polymer, comprising the reaction product of components (a), (b), and optionally (c), wherein components (a), (b), and (c) are:
(a) at least one diamine of Structure (I):

(b) at least one tetracarboxylic acid dianhydride, and optionally,
(c) at least one compound containing a first functional group reactive with an amine or an anhydride and at least one second functional group selected from the group consisting of an unsubstituted alkenyl group and an unsubstituted alkynyl group, wherein the first functional group reactive to an amine is selected from the group consisting of an anhydride group, an acid halide group, an epoxy group, and an isocyanate group and the first functional group reactive to an anhydride is selected from the group consisting of an amino group, a hydroxyl group, and a thiol group,
wherein each of R 6 , R 7 , R 8 , R 9 and R 10 , independently, is H, an unsubstituted C 1 -C 6 linear or branched alkyl group, or an unsubstituted C 5 -C 8 cycloalkyl group, each R 11 , independently, is H, an unsubstituted C 1 -C 6 linear or branched alkyl group, or an unsubstituted C 5 -C 8 cycloalkyl group; each R 12 , independently, is H, an unsubstituted C 1 -C 6 linear or branched alkyl group, or an unsubstituted C 5 -C 8 cycloalkyl group; x is an integer from 0 to 3; y is an integer from 0 to 2; and each z, independently, is an integer from 1 to 4.

12. The polymer of claim 11 , wherein the —O—(CH 2 ) z —CH═CH 2 group on the indane moiety is at the para position relative to the group —C(R 9 R 10 )— and the other —O—(CH 2 ) z —CH═CH 2 group is at the para position relative to the indane moiety.

13. The polymer of claim 11 , wherein the —NH 2 group on the indane moiety is at the ortho position relative to the —O—(CH 2 ) z —CH═CH 2 group on the indane moiety and the —NH 2 group on the phenyl moiety is at the ortho position relative to the —O—(CH 2 ) z —CH═CH 2 group on the phenyl moiety.

14. The polymer of claim 11 , wherein each of R 6 , R 9 , and R 10 is a unsubstituted C 1 -C 6 linear or branched alkyl group.

15. The polymer of claim 14 , wherein each of R 6 , R 9 , and R 10 is CH 3 , CH 2 CH 3 , or CH(CH 3 ) 2 .

16. The polymer of claim 11 , wherein x is 0 or 1, y is 0 or 1, R 7 is H, and R 8 is H.

17. The polymer of claim 11 , wherein the diamine of Structure (I) is selected from the group consisting of:

18. The polymer of claim 11 , wherein tetracarboxylic acid dianhydride is selected from a group consisting of:

19. A composition, comprising:
(A) at least one polyimide polymer of claim 1 ;
(B) at least one reactive functional compound (RFC) having at least one functional group capable of reacting with an unsubstituted alkenyl group or an unsubstituted alkynyl group on the polyimide polymer wherein the at least one functional group is selected from the group consisting of a vinyl group, an allyl group, a vinyl ether group, a propenyl ether group, a (meth)acryloyl group, an epoxy group, a SiH group, and a thiol group;
(C) an initiator capable of initiating a reaction between an unsubstituted alkenyl group or an unsubstituted alkynyl group on the polyimide polymer and the RFC; and
(D) at least one solvent.

20. A process, comprising coating a substrate with the composition of claim 19 to form a coated substrate having a film on the substrate, and baking the coated substrate to form a coated substrate having a dried film.

21. The process of claim 20 , wherein the coated substrate is baked at a temperature from about 50° C. to about 200° C.

22. The process of claim 21 , further comprising exposing the dried film to radiation through a mask to form a coated substrate having a dried, patternwise exposed film.

23. The process of claim 22 , further comprising baking the dried, patternwise exposed film at a temperature from about 50° C. to about 150° C. in a second baking step.

24. The process of claim 23 , further comprising developing a portion of the dried, exposed film in a developer to produce a relief image on the substrate.

Assignees

• Fujifilm Electronic Mat Usa Inc

Inventors

• Malik Sanjay
• Reinerth William A
• De Binod B
• Sakamuri Raj
• Dimov Ognian N
• Naiini Ahmad A

Classifications

• C08G69/32

  from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound · CPC title

• C08G73/14 Primary

  Polyamide-imides · CPC title

• C08L79/08

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

• C08G73/1078 Primary

  wholly aromatic in the diamino moiety · CPC title

• G03F7/0387

  Polyamides or polyimides · CPC title