NOVEL POLYIMIDE PRECURSOR COMPOSITION, USE THEREOF AND PRODUCTION METHOD THEREOF

• US 20100084171A1
• Filed: 12/19/2007
• Published: 04/08/2010
• Est. Priority Date: 12/26/2006
• Status: Active Grant

• Current Assignee: Kaneka Corporation
• Original Assignee: Kaneka Corporation
• Inventors: Sekito, Yoshihide, Fujihara, Kan, Kogiso, Tetsuya
• Granted Patent: US 8,754,186 B2
• Time in Patent Office: Days
• US Class Current: 174/258
• CPC Class Codes: C08G 73/1007 from tetracarboxylic acids or derivatives and diamines
• 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 73/106 containing silicon
• CPC Class Codes: C08G 73/1064 containing sulfur
• CPC Class Codes: C08G 73/1075 Partially aromatic polyimides
• CPC Class Codes: C08G 73/1082 wholly aromatic in the tetracarboxylic moiety
• CPC Class Codes: C08L 79/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: C09D 179/08 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: H05K 3/287 Photosensitive compositions

Abstract

An object of the present invention is to provide a polyimide precursor composition that can be cured at low temperatures (250° C. or lower), while having a low viscosity even at a high concentration, and a method of producing the same. Another object of the present invention is to provide a polyimide coating film obtained from the polyimide precursor composition and having good physical properties, and a method of producing the same. Furthermore, another object of the present invention is to provide a photosensitive resin composition containing the polyimide precursor composition, and a method of producing the same. These objects can be achieved by the polyimide precursor composition containing an imidized tetracarboxylic acid having a specific structure and a diamine having a specific structure.

Claims

1. A polyimide precursor composition comprising:

at least an imidized tetracarboxylic acid represented by general formula (1) below;

(wherein Rs each independently represent a tetravalent organic group, R′

s each independently represent a divalent organic group, and 1 represents an integer of 0 to

     20); and

a diamine represented by general formula (2) below;

[Chem. 2]

H₂N—

R″

—

NH₂ 

 

General formula (2)

(wherein R″

represents a divalent organic group.)

2. The polyimide precursor composition according to claim 1, wherein each of Rs in general formula (1) above is a tetravalent organic group selected from general formula group (1) below:

3. The polyimide precursor composition according to claim 1, wherein each of R′

s in general formula (1) above at least includes a divalent organic group represented by general formula group (2) below;

(wherein o, p, and q each independently represent an integer of 1 to 30, R1 and R2 each independently represent an alkyl group having 1 to 12 carbon atoms or an aromatic group, m represents an integer of 1 to 40, n represents an integer of 1 to 20, and R3 and R4 each independently represent an alkyl group having 1 to 12 carbon atoms.)

4. The polyimide precursor composition according to claim 1, wherein R″

in general formula (2) above is a divalent organic group selected from general formula group (3) below;

(wherein o, p, and q each independently represent an integer of 1 to 30, R1 and R2 each independently represent an alkyl group having 1 to 12 carbon atoms or an aromatic group, m represents an integer of 1 to 40, n represents an integer of 1 to 20, and R3 and R4 each independently represent an alkyl group having 1 to 12 carbon atoms.)

5. A polyimide precursor composition solution produced by dissolving the polyimide precursor composition according to claim 1 so that a solute concentration is 40 to 90 weight percent.

6. A polyimide coating film obtained from the polyimide precursor composition according to claim 1 or a polyimide precursor composition solution produced by dissolving the polyimide precursor composition according to claim 1 so that a solute concentration is 40 to 90 weight percent.

7. A printed wiring board having a polyimide coating film, the printed wiring board produced by coating the polyimide precursor composition according to claim 1 or a polyimide precursor composition solution produced by dissolving the polyimide precursor composition according to claim 1 so that a solute concentration is 40 to 90 weight percent on a printed wiring board, and imidizing by heating.

8. A photosensitive resin composition comprising the polyimide precursor composition according to claim 1, and at least a photosensitive resin, and a photopolymerization initiator.

9. A method of producing a polyimide precursor composition comprising the steps of:

conducting a reaction between a tetracarboxylic dianhydride represented by general formula (3) below;

(wherein R represents a tetravalent organic group), and

a diamine represented by general formula (4) below;

[Chem. 7]

H₂N—

R′

—

NH₂ 

 

General formula (4)

(wherein R'"'"' represents a divalent organic group)

in a ratio in which the diamine represented by general formula (4) is 0.20 to 0.80 moles relative to 1 mole of the tetracarboxylic dianhydride represented by general formula (3) to prepare an amic acid;

imidizing the amic acid to prepare an imide; and

reacting the imide with water to prepare an imidized tetracarboxylic acid the inner part of which is imidized and each terminal of which has a tetracarboxylic acid structure,

wherein the method further includes a step of mixing the imidized tetracarboxylic acid prepared in the above step with a diamine represented by general formula (2) below;

[Chem. 8]

H₂N—

R″

—

NH₂ 

 

General formula (2)

(wherein R″

represents a divalent organic group)

in a ratio in which the total of the diamine represented by general formula (2) and the diamine represented by general formula (4) used in the step of preparing the amic amid is 0.70 to 1.30 moles relative to 1 mole of the imidized tetracarboxylic acid.

10. The method of producing a polyimide precursor composition according to claim 9, wherein the diamine represented by general formula (4) at least includes a diamine represented by general formula group (4) below:

(wherein o, p, and q each independently represent an integer of 1 to 30, R1 and R2 each independently represent an alkyl group having 1 to 12 carbon atoms or an aromatic group, m represents an integer of 1 to 40, n represents an integer of 1 to 20, and R3 and R4 each independently represent an alkyl group having 1 to 12 carbon atoms.)

11. A method of producing a polyimide precursor composition solution comprising a step of dissolving the polyimide precursor composition produced by the method according to claim 9 in an organic solvent so that a solute concentration is 40 to 90 weight percent.

12. A method of producing a polyimide coating film comprising a step of obtaining a polyimide coating film from the polyimide precursor composition produced by the method according to claim 9 or a polyimide precursor composition solution produced by the method of dissolving the polyimide precursor composition produced by the method according to claim 9 in an organic solvent so that a solute concentration is 40 to 90 weight percent.

13. A method of producing a printed wiring board having a polyimide coating film, comprising the steps of coating the polyimide precursor composition produced by the method according to claim 9 or a polyimide precursor composition solution produced by the method of dissolving the polyimide precursor composition produced by the method according to claim 9 in an organic solvent so that a solute concentration is 40 to 90 weight percent on a printed wiring board, and imidizing by heating.

14. A method of producing a photosensitive resin composition comprising a step of mixing the polyimide precursor composition produced by the method according to claim 9 with at least a photosensitive resin, and a photopolymerization initiator.