NOVEL POLYIMIDE PRECURSOR COMPOSITION AND USE THEREOF

• US 20100132989A1
• Filed: 04/03/2008
• Published: 06/03/2010
• Est. Priority Date: 04/19/2007
• Status: Abandoned Application

• Current Assignee: Kaneka Corporation
• Original Assignee: Kaneka Corporation
• Inventors: Fujihara, Kan, Kogiso, Tetsuya, Sekito, Yoshihide
• Application Number:
  US12/596,027
• Publication Number:
  US 20100132989A1
• Time in Patent Office: Days
• US Class Current: 174/258
• 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 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/346 having four carboxylic acid groups
• CPC Class Codes: C08G 18/4858 Polyethers containing oxyalkylene groups having more than four carbon atoms in the alkylene group
• CPC Class Codes: C08G 18/6625 with compounds of group C08G18/34
• CPC Class Codes: C08G 73/1035 from tetracarboxylic acids or derivatives and diisocyanates
• CPC Class Codes: C08G 73/1067 Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
• CPC Class Codes: C08G 73/14 Polyamide-imides
• CPC Class Codes: C08G 73/16 Polyester-imides
• CPC Class Codes: C08J 2379/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: C08J 3/28 Treatment by wave energy or particle radiation
• CPC Class Codes: C08J 5/18 Manufacture of films or sheets
• CPC Class Codes: C08L 79/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: G03F 7/027 Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds G03F7/075 takes precedence
• CPC Class Codes: G03F 7/037 the binders being polyamides or polyimides
• CPC Class Codes: H05K 3/287 Photosensitive compositions

Abstract

An object of the present invention is to provide a polyimide precursor composition solution that (i) uses no siloxane diamine, (ii) is curable at low temperature (not more than 250° C.) and (iii) has low viscosity regardless of its high concentration, and a photosensitive resin composition, photosensitive resin film, a thermosetting resin composition, a polyimide insulating film, and a printed wiring board with an insulating film, each of which has good physical properties and is obtained by use of the polyimide precursor composition solution. The foregoing object is attained by using a polyimide precursor composition solution which includes at least a (A) urethane imide oligomer having a terminal carboxylic acid group and a (B) diamino compound and/or isocyanate compound.

Claims

1. A polyimide precursor composition comprising at least:

a (A) urethane imide oligomer having a terminal carboxylic acid group; and

a (B) diamino compound and/or isocyanate compound.

2. The polyimide precursor composition according to claim 1, wherein the (A) urethane imide oligomer having a terminal carboxylic acid group is a tetracarboxylic acid urethane imide oligomer.

3. The polyimide precursor composition according to claim 1, wherein the (A) urethane imide oligomer having a terminal carboxylic acid group is obtainable 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 synthesized terminal isocyanate compound with a (c) tetracarboxylic acid dianhydride represented by a general formula (3) so as to synthesize a urethane imide oligomer having a terminal acid anhydride, and (iii) reacting the synthesized urethane imide oligomer having a terminal acid anhydride with (d) water and/or primary alcohol, the (a) diol compound being represented by the following general formula (1):

Chem 1

HO

R

_IOH 

 

general formula (1)

where R denotes a bivalent organic group; and

I denotes an integer of 1 to 20,

the (b) diisocyanate compound being represented by the following general formula (2);

Chem. 2

O═

C═

N—

X—

N═

C═

O 

 

general formula (2)

where X denotes a bivalent organic group, and

the (c) tetracarboxylic acid dianhydride being represented by the following general formula (3);

4. The polyimide precursor composition according to claim 1, wherein the (a) diol compound includes at least a polycarbonate diol represented by the following general formula (4):

5. The polyimide precursor composition according to claim 1, wherein the (A) urethane imide oligomer having a terminal carboxylic acid group further includes a carboxyl group in its side chain.

6. A photosensitive resin composition comprising at least:

a polyimide precursor composition as set forth in claim 1;

a (C) photosensitive resin; and

a (D) photopolymerization initiator.

7. The photosensitive resin composition according to claim 6, wherein the (A) urethane imide oligomer having a terminal carboxylic acid group, the (B) diamino compound and/or isocyanate compound, the (C) photosensitive resin, and the (D) photopolymerization initiator are included in the photosensitive resin composition in such a manner that the (C) photosensitive resin is included by 10 parts by weight to 200 parts by weight and the (D) photopolymerization initiator is included by 0.1 parts by weight to 50 parts by weight, with respect to a total solid content of the (A) urethane imide oligomer having a terminal carboxylic acid and the (B) diamino compound and/or isocyanate compound being 100 parts by weight.

8. The photosensitive resin composition according to claim 6, further comprising a (E) thermosetting resin.

9. The photosensitive resin composition according to claim 8, wherein the (E) thermosetting resin is comprised by 0.5 parts by weight to 100 parts by weight, with respect to a total solid content of the (A) urethane imide oligomer having a terminal carboxylic acid group, the (B) diamino compound and/or isocyanate compound, the (C) photosensitive resin, and the (D) photopolymerization initiator being 100 parts by weight.

10. A thermosetting resin composition comprising at least:

a polyimide precursor composition as set forth in claim 1; and

a (E) thermosetting resin.

11. The thermosetting resin composition according to claim 10, wherein the (E) thermosetting resin is comprised by 0.5 parts by weight to 100 parts by weight, with respect to a total solid content of the (A) urethane imide oligomer having a terminal carboxylic acid group, and the (B) diamino compound and/or isocyanate compound being 100 parts by weight.

12. A polyimide precursor composition solution obtained by dissolving into an organic solvent a polyimide precursor composition as set forth in claim 1.

13. A resin film obtained by (i) applying to a substrate surface a polyimide precursor composition solution as set forth in claim 12, then (ii) drying the applied solution.

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

15. A printed wiring board with an insulating film, in which the insulating film is an insulating film as set forth in claim 14 and covers the printed wiring board.

16. A polyimide precursor composition solution obtained by dissolving into an organic solvent a photosensitive resin composition as set forth in claim 6.

17. A polyimide precursor composition solution obtained by dissolving into an organic solvent a thermosetting resin composition as set forth in claim 10.