Polyimides

Patent metadata

Field	Value
Publication number	US-11939428-B2
Application number	US-202117391298-A
Country	US
Kind code	B2
Filing date	Aug 2, 2021
Priority date	Oct 25, 2016
Publication date	Mar 26, 2024
Grant date	Mar 26, 2024

Abstract

This disclosure relates to a polyimide polymer that includes the reaction product of: (a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib),

(b) at least one diamine of Structure (II),

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

First claim

What is claimed is:

1. A polyimide polymer, comprising the reaction product of components (a), (b), (c), and (d), wherein components (a), (b), (c), and (d) are:
(a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib):

wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13, and R 14 ndependently, is H, a substituted or unsubstituted C 1 -C 6 linear or branched alkyl group, or a substituted or unsubstituted C 5 -C 7 cycloalkyl group,
(b) at least one diamine selected from the group consisting of a diamine of Structure (IIb) and a diamine of Structure (IIc):

wherein each R 20, independently, is a hydrogen atom, a substituted or unsubstituted C 1 -C 6 linear or branched alkyl group, or a substituted or unsubstituted phenyl group, each R 22, independently, is a substituted or unsubstituted C 1 -C 6 linear or branched alkylene group, R 23 is a substituted or unsubstituted C 1 -C 20 linear or branched alkyl group or a C 6 -C 20 substituted or unsubstituted aryl group, and R 24 is a S atom, —NR 25 —, —CH(R 25 )—, or —(CH 2 ) 2 —, in which R 25 is a C 1 -C 6 substituted or unsubstituted linear or branched alkyl group,
(c) at least one tetracarboxylic acid dianhydride, and
(d) at least one compound comprising a first functional group reactive with an amine or an anhydride and at least a second functional group selected from the group consisting of a substituted or unsubstituted alkenyl group and a substituted or unsubstituted alkynyl group.

2. The polymer of claim 1 , wherein component (a) comprises at least one diamine of Structure (Ia).

3. The polymer of claim 2 , wherein the amino group on the indane ring in Structure (Ia) is at the 5 position and the other amino group in Structure (Ia) is at the 4 position.

4. The polymer of claim 3 , wherein each of R 1 , R 2 , and R 3 is CH 3 and each of R 4 and R 5 is H.

5. The polymer of claim 1 , wherein component (b) comprises a diamine of Structure (IIb).

6. The polymer of claim 1 , wherein component (b) comprises a diamine of Structure (IIc).

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

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

9. A polyamic acid polymer, comprising the reaction product of components (a), (b), (c), and (d), wherein components (a), (b), (c), and (d) are:
(a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib):

wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , and R 14 independently, is H, a substituted or unsubstituted C 1 -C 6 linear or branched alkyl group, or a substituted or unsubstituted C 5 -C 7 cycloalkyl group,
(b) at least one diamine selected from the group consisting of a diamine of Structure (IIb) and a diamine of Structure (IIc):

wherein each R 20 , independently, is a hydrogen atom, a substituted or unsubstituted C 1 -C 6 linear or branched alkyl group, or a substituted or unsubstituted phenyl group, each R 22 , independently, is a substituted or unsubstituted C 1 -C 6 linear or branched alkylene group, R 23 is a substituted or unsubstituted C 1 -C 20 linear or branched alkyl group or a C 5 -C 20 substituted or unsubstituted aryl group, and R 24 is a O or S atom, —NR 25 —, —CH(R 25 )—, or —(CH 3 ) 2 —, in which R 25 is a C 1 -C 6 substituted or unsubstituted linear or branched alkyl group,
(c) at least one tetracarboxylic acid dianhydride, and
(d) at least one compound comprising a first functional group reactive with an amine or an anhydride and at least a second functional group selected from the group consisting of a substituted or unsubstituted alkenyl group and a substituted or unsubstituted alkynyl group.

10. The polyamic acid polymer of claim 9 , wherein component (b) comprises the diamine of Structure (IIb).

11. The polyamic acid polymer of claim 9 , wherein component (b) comprises the diamine of Structure (IIc).

12. 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 a substituted or unsubstituted alkenyl group or a substituted or unsubstituted alkynyl group on the polyimide polymer;
(C) an initiator capable of initiating a reaction between the substituted or unsubstituted alkenyl group or a substituted or unsubstituted alkynyl group on the polyimide polymer and the RFC; and
(D) at least one solvent.

13. The compositions of claim 12 , wherein component (b) comprises a diamine of Structure (IIb).

14. The compositions of claim 13 , wherein component (b) comprises a diamine of Structure (IIc).

15. A process, comprising:
coating a substrate with the composition of claim 12 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.

16. The process of claim 15 , wherein the coated substrate is baked at a temperature from about 50° C. to about 200° C.

17. The process of claim 16 , further comprising exposing the dried film to radiation through a mask to form a coated substrate having a dried, patternwise exposed film.

18. The process of claim 17 , further comprising baking the dried, patternwise exposed film at a temperature from about 50° C. to about 150° C. in a second baking step.

19. The process of claim 18 , further comprising developing a portion of the dried, exposed film in a developer to produce a relief image on the substrate.

20. The process of claim 19 , further comprising rinsing the relief image on the substrate with a solvent or a mixture of solvents.

21. The process of claim 20 , further comprising baking the substrate having a relief image at a temperature from about 50° C. to about 200° C. in a third baking step.

22. An article formed by a process comprising coating a substrate with the composition of claim 14 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,
wherein the article is a semiconductor substrate, a flexible film for electronics, a wire isolation, a wire coating, a wire enamel, or an inked substrate.

23. A semiconductor device, comprising the article of claim 22 .

24. The semiconductor device of claim 23 , wherein the semiconductor device is an integrated circuit, a light emitting diode, a solar cell, and a transistor.

25. A dry film structure, comprising a carrier substrate, a protective layer, and a polymeric layer between the carrier substrate and the protective layer, wherein the polymeric layer contains:
(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 a substituted or unsubstituted alkenyl group or a substitu

Assignees

• Fujifilm Electronic Mat Usa Inc

Inventors

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

Classifications

• H10W74/40 Primary

  characterised by their materials · CPC title

• C08G73/1067 Primary

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

• C08G73/1085

  Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties · CPC title

• C08G73/12

  Unsaturated polyimide precursors · CPC title

• C08L79/08

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