Active energy ray-curable polyimide resin composition

• US 20030130475A1
• Filed: 06/27/2002
• Published: 07/10/2003
• Est. Priority Date: 06/28/2001
• Status: Active Grant

• Current Assignee: Dainippon Ink and Chemicals Incorporated
• Original Assignee: Dainippon Ink and Chemicals Incorporated
• Inventors: Yamashina, Yohzoh, Ichinose, Eiju, Ishikawa, Hidenobu
• Granted Patent: US 6,784,275 B2
• Time in Patent Office: Days
• US Class Current: 528/171
• CPC Class Codes: C08G 73/1035 from tetracarboxylic acids or derivatives and diisocyanates
• CPC Class Codes: C08G 73/14 Polyamide-imides
• CPC Class Codes: G03F 7/0387 Polyamides or polyimides
• CPC Class Codes: H05K 3/4676 Single layer compositions

Abstract

Disclosed is an active energy ray-curable polyimide resin composition which comprises a polymerizable polyimide resin (I) having an isocyanurate ring, an alicyclic structure, an imide ring and a (meth)acryloyl group and being capable of patterning with a dilute alkali aqueous solution.

Claims

1. An active energy ray-curable polyimide resin composition which comprises a polymerizable polyimide resin (I) having an isocyanurate ring, an alicyclic structure, an imide ring and a (meth)acryloyl group and being capable of patterning with a dilute alkali aqueous solution.

2. The active energy ray-curable polyimide resin composition according to claim 1, wherein the polymerizable polyimide resin (I) has a concentration of isocyanurate ring of 0.4 to 1.2 mmol/g, a concentration of (meth)acryloyl group of 0.3 to 4 mmol/g, an acid value of 20 to 250, a number average molecular weight of 1,000 to 20,000, and a weight average molecular weight of 1,500 to 30,000.

3. The active energy ray-curable polyimide resin composition according to claim 1, which further contains an organic solvent (II), an epoxy compound (III) and a photo-initiator (IV).

4. The active energy ray-curable polyimide resin composition according to claim 1, which further contains an organic solvent (II), an epoxy compound (III), a photo-initiator (IV), and a reactive diluent (V).

5. The active energy ray-curable polyimide resin composition according to claim 1 or 3, wherein the polymerizable polyimide resin (I) is obtainable by a process comprising reacting a polyisocyanate compound (A) comprising an isocyanurate ring-containing polyisocyanate compound (A1) derived from an alicyclic diisocyanate compound and/or a urethane prepolymer (A2) having an isocyanate group at the terminal and being obtainable from the polyisocyanate compound (A1) and a polyol compound (a2), with an anhydride (B) of polycarboxylic acid having three or more carboxyl groups in an organic solvent, and successively with a compound (C1) having a (meth)acryloyl group and a hydroxyl group and/or a compound (C2) having a (meth)acryloyl group and an epoxy group.

6. The active energy ray-curable polyimide resin composition according to claim 5, wherein the polymerizable polyimide resin (I) is obtainable by reacting the polyisocyanate compound (A) with an acid anhydride having a carboxyl group as the polycarboxylic acid anhydride (B) and successively with the compound (C1) having a (meth)acryloyl group and a hydroxyl group and/or the compound (C2) having a (meth)acryloyl group and an epoxy group, or by reacting the polyisocyanate compound (A) with an acid anhydride having no carboxyl group as the polycarboxylic acid anhydride (B) and successively with the compound (C1) having a (meth)acryloyl group and a hydroxyl group.

7. The active energy ray-curable polyimide resin composition according to claim 5, wherein the polyisocyanate compound (A1) comprises a triisocyanate compound having one isocyanurate ring in an amount of 30% by weight or more.

8. The active energy ray-curable polyimide resin composition according to claim 5, wherein the polymerizable polyimide resin (I) is obtainable by adding, in the course of the reaction between the polyisocyanate compound (A) and the polycarboxylic acid anhydride (B), the compound (C1) having a (meth)acryloyl group and a hydroxyl group so that the ratio (n_c1)/(n_ab) of the molar amount (n_c1) of the hydroxyl group in the compound (C1) to the total molar amount (n_ab) of the acid anhydride group and isocyanate group remaining in the reaction system is in the range of 0.9-to 2.0, and reacting them.

9. The active energy ray-curable polyimide resin composition according to claim 5, wherein the urethane prepolymer (A2) is obtainable by reacting the polyisocyanate compound (A1) and a polyol compound comprising a polyol (a21) having a carboxyl group, in such a molar ratio that the isocyanate group in the polyisocyanate compound (A1) is in excess of the hydroxyl group in the polyol compound.

10. The active energy ray-curable polyimide resin composition according to claim 5, wherein the polymerizable polyimide resin (I) is obtainable by using a tricarboxylic acid anhydride and/or a tetracarboxylic acid anhydride as the polycarboxylic acid anhydride (B) and using a compound having two to five (meth)acryloyl groups and one hydroxyl group as the compound (C1) having a (meth)acryloyl group and a hydroxyl group and/or the compound (C2) having a (meth)acryloyl group and an epoxy group.

11. The active energy ray-curable polyimide resin composition according to claim 6, wherein the organic solvent is a polar solvent containing neither nitrogen atom nor sulfur atom and capable of dissolving the polymerizable polyimide resin (I).