Polyimide precursor composition and use thereof

• US 9,267,004 B2
• Filed: 07/15/2009
• Issued: 02/23/2016
• Est. Priority Date: 07/22/2008
• Status: Active Grant

• Current Assignee: Kaneka Corporation
• Original Assignee: Kaneka Corporation
• Inventors: Okada, Koji, Sekito, Yoshihide
• Primary Examiner(s): Willis, Tremesha S
• Application Number:
  US12/997,151
• Publication Number:
  US 20110083884A1
• Time in Patent Office: 2,414 Days
• Field of Search: 174/256, 174/250, 174/255, 174/258, 528/84
• US Class Current: 1/1
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/346 having four carboxylic acid groups
• CPC Class Codes: C08G 18/348 Hydroxycarboxylic acids
• CPC Class Codes: C08G 18/44 Polycarbonates
• CPC Class Codes: C08G 73/1007 from tetracarboxylic acids or derivatives and diamines
• CPC Class Codes: C08G 73/1035 from tetracarboxylic acids or derivatives and diisocyanates
• CPC Class Codes: C08G 73/1042 Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
• CPC Class Codes: C08G 73/1046 Polyimides containing oxygen in the form of ether bonds in the main chain
• CPC Class Codes: C08G 73/105 with oxygen only in the diamino moiety
• CPC Class Codes: C08G 73/1067 Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
• CPC Class Codes: C08G 73/1071 Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
• CPC Class Codes: C08G 73/16 Polyester-imides
• CPC Class Codes: C08L 79/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: G03F 7/037 the binders being polyamides or polyimides
• CPC Class Codes: G03F 7/40 Treatment after imagewise removal, e.g. baking
• CPC Class Codes: H05K 1/0393 Flexible materials H05K1/038 takes precedence; specific organic compositions are classified in H05K1/0313 and subgroups
• CPC Class Codes: H05K 3/287 Photosensitive compositions

Abstract

An object of the present invention is to provide (a) a polyimide precursor solution which is curable at low temperatures (not more than 200° C.) and which has excellent long-term storage stability, (b) a photosensitive resin composition, a photosensitive resin film, a thermosetting resin composition, and a polyimide insulating film, each of which is obtainable from the polyimide precursor solution and each of which is preferably usable as an insulating material for electric and electronic purposes, and (c) a printed wiring board provided with the insulating film. The above object is achievable by use of a polyimide precursor composition solution containing at least a partially imidized polyimide precursor having a urethane bond.

Claims

1. A partially imidized polyimide precursor compound at least having a urethane bond, an imide bond, a polyamide acid structure, and a polycarbonate skeleton.

2. The polyimide precursor compound as set forth in claim 1, which is obtained by (i) reacting at least a (a) diol compound and a (b) diisocyanate compound so as to synthesize a terminal isocyanate compound, (ii) reacting the terminal isocyanate compound with a (c) tetracarboxylic acid dianhydride so as to synthesize a urethane imide oligomer having a terminal acid anhydride, and (iii) carrying out an addition reaction of the urethane imide oligomer having a terminal acid anhydride, with a (d) diamine, the (a) diol compound being represented by General Formula (1):

[Chem. 1]

HO—

R—

OH 

 

(1)

(wherein R represents a divalent organic group),

the (b) diisocyanate compound being represented by General Formula (2);

[Chem. 2]

O═

C═

N—

X—

N═

C═

O 

 

(2)

(wherein X represents a divalent organic group),

the (c) tetracarboxylic acid dianhydride being represented by General Formula (3);

3. The polyimide precursor compound as set forth in claim 2, wherein:

the (a) diol compound contains at least a polycarbonate diol represented by General Formula (5);

4. The polyimide precursor compound as set forth in claim 1, which further has a carboxyl group in its side chain.

5. A photosensitive resin composition containing at least:

the (A) partially imidized polyimide precursor compound, as set forth in claim 1;

a (B) photosensitive resin; and

a (C) photopolymerization initiator.

6. The photosensitive resin composition as set forth in claim 5, wherein the (A) partially imidized polyimide precursor compound, the (B) photosensitive resin, and the (C) photopolymerization initiator are contained in the photosensitive resin composition such that the (B) photosensitive resin and the (C) photopolymerization initiator are contained by 10 to 200 parts by weight and by 0.1 to 50 parts by weight, respectively, relative to 100 parts by weight of a solid content of the (A) partially imidized polyimide precursor.

7. The photosensitive resin composition as set forth in claim 5, further containing a (D) thermosetting resin.

8. The photosensitive resin composition as set forth in claim 7, wherein:

the (D) thermosetting resin is contained in the photosensitive resin composition by 0.5 to 100 parts by weight relative to 100 parts by weight of a total solid content of the (A) partially imidized polyimide precursor compound, the (B) photosensitive resin, and the (C) photopolymerization initiator.

9. A thermosetting resin composition containing at least:

the (A) partially imidized polyimide precursor compound, as set forth in claim 1; and

a (D) thermosetting resin.

10. The thermosetting resin composition as set forth in claim 9, wherein:

the (D) thermosetting resin is contained in the thermosetting resin composition by 0.5 to 100 parts by weight relative to 100 parts by weight of a solid content of the (A) partially imidized polyimide precursor compound.

11. A polyimide precursor composition solution obtained by dissolving, in an organic solvent, the partially imidized polyimide precursor compound, as set forth in claim 1.

12. A resin film obtained by applying, to a surface of a base material, a polyimide precursor composition solution as set forth in claim 11, and drying the polyimide precursor composition solution thus applied.

13. An insulating film obtained by curing a resin film as set forth in claim 12.

14. A printed wiring board provided with an insulating film, wherein:

the insulating film is an insulating film as set forth in claim 13; and

the printed wiring board is covered with the insulating film.

15. A polyimide precursor composition solution obtained by dissolving, in an organic solvent, a photosensitive resin composition as set forth in claim 5.

16. A resin film obtained by applying, to a surface of a base material, a polyimide precursor composition solution as set forth in claim 15, and drying the polyimide precursor composition solution thus applied.

17. An insulating film obtained by curing a resin film as set forth in claim 16.

18. A printed wiring board provided with an insulating film, wherein:

the insulating film is an insulating film as set forth in claim 17; and

the printed wiring board is covered with the insulating film.

19. A polyimide precursor composition solution obtained by dissolving, in an organic solvent, a thermosetting resin composition as set forth in claim 9.

20. A resin film obtained by applying, to a surface of a base material, a polyimide precursor composition solution as set forth in claim 19, and drying the polyimide precursor composition solution thus applied.

21. An insulating film obtained by curing a resin film as set forth in claim 20.

22. A printed wiring board provided with an insulating film, wherein:

the insulating film is an insulating film as set forth in claim 21; and

the printed wiring board is covered with the insulating film.

23. A partially imidized polyimide precursor compound, having:

(i) at least one repeating unit having a urethane bond, the repeating unit being represented by General Formula (6);