Polyimide precursor composition and use thereof

Patent metadata

Field	Value
Publication number	US-9267004-B2
Application number	US-99715109-A
Country	US
Kind code	B2
Filing date	Jul 15, 2009
Priority date	Jul 22, 2008
Publication date	Feb 23, 2016
Grant date	Feb 23, 2016

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.

First claim

The invention claimed is:

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):

(wherein Y represents a tetravalent organic group), and
the (d) diamine being represented by General Formula (4):
[Chem. 4]
H 2 N- z -NH 2   (4)

(wherein Z represents a divalent organic group).

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):

(wherein each R 1 independently represents a divalent organic group; and m represents an integer of 1 to 20).

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):

wherein R and X each independently represent a divalent organic group; and m represents an integer of not less than 1;
(ii) imide bond represented by General Formula (7):

wherein R 2 independently represents a divalent organic group; each Y independently represents a tetravalent organic group; and n represents an integer of not less than 1;
(iii) a polyamide acid structure represented by General Formula (8):

wherein Z independently represents a divalent organic group; each Y independently represents a tetravalent organic group; and p represents an integer of not less than 1; and
(iv) a polycarbonate skeleton.

Assignees

• Okada Koji
• Sekito Yoshihide
• Kaneka Corp

Inventors

• Okada Koji
• Sekito Yoshihide

Classifications

• C08L79/08

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

• C08G73/1035 Primary

  from tetracarboxylic acids or derivatives and diisocyanates · CPC title

• H05K3/287

  Photosensitive compositions · CPC title

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title

• C08G73/16

  Polyester-imides · CPC title