Resin composition, cured film, laminated film, and method for manufacturing semiconductor device

Patent metadata

Field	Value
Publication number	US-9716026-B2
Application number	US-201314430361-A
Country	US
Kind code	B2
Filing date	Sep 25, 2013
Priority date	Sep 25, 2012
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

[Problem] To provide a highly heat resistant resin composition which exhibits good tackiness at low temperatures less than or equal to 180° C., and whose production of a volatile portion due to decomposition or the like is small even at high temperatures greater than or equal to 250° C., and whose increase in adhesive force is small even after passage through a heat treatment step, and therefore which allows a base material to be easily peeled off at room temperature when the base material is to be peeled off, and a cured membrane and a laminate film that employ this resin composition.
[Solution Means] A resin composition containing a polyimide-based resin and a methylol-based compound, the resin composition being characterized in that the polyimide-based resin has an acid dianhydride residue and a diamine residue, and has as the diamine residue at least a residue of a polysiloxane-based diamine represented by General formula (1) and a residue of an aromatic diamine having a hydroxyl group, and a cured product and a laminate film that employ this resin composition.

(n is a natural number, and an average value thereof calculated from an average molecular weight of the polysiloxane-based diamine is in a range of 5 to 30. R 1 and R 2 may be individually the same or different, indicating an alkylene group or a phenylene group whose carbon number is 1 to 30. R 3 to R 6 may be individually the same or different, indicating an alkyl group, a phenyl group or a phenoxy group whose carbon number is 1 to 30.)

First claim

The invention claimed is:

1. A resin composition containing a polyimide-based resin and a methylol-based compound, wherein
the polyimide-based resin has an acid dianhydride residue and a diamine residue;
the diamine residue is at least a residue of a polysiloxane-based diamine represented by general formula (1) and a residue of an aromatic diamine having an hydroxyl group,

wherein n is a natural number, and an average value thereof calculated from an average molecular weight of the polysiloxane-based diamine is in a range of 5 to 30, R 1 and R 2 may be individually the same or different and indicate an alkylene group or a phenylene group having a carbon number that is 1 to 30, R 3 to R 6 may be individually the same or different and indicate an alkyl group, a phenyl group or a phenoxy group having a carbon number that is 1 to 30; and
the resin composition has a glass transition temperature after curing that is less than or equal to 40° C.

2. The resin composition according to claim 1 , containing as the diamine residue the residue of the polysiloxane-based diamine represented by general formula (1) at greater than or equal to 40 mol % in a total amount of the diamine residue.

3. The resin composition according to claim 1 , containing as the diamine residue the residue of the aromatic diamine having a hydroxyl group at 1 to 40 mol % in a total amount of the diamine residue.

4. The resin composition according to claim 3 , wherein the aromatic diamine having an hydroxyl group is an aromatic diamine represented by any one of General formulas (2) to (5) below:

wherein at least one of R 7 to R 10 is a hydroxyl group, and the others may be the same or different, indicating a group selected from a hydrogen atom, an alkyl group having a carbon number that is 1 to 30, an alkoxy group having a carbon number that is 1 to 30, a halogen, a carboxyl group, a sulfone group, a nitro group, and a cyano group;

wherein X 1 indicates a group selected from a direct bond, O, S, SO, SO 2 , CO, CH 2 , C(CH 3 ) 2 and C(CF 3 ) 2 , at least one of R 11 to R 18 is a hydroxyl group, and the others may be the same or different, indicating a group selected from a hydrogen atom, an alkyl group having a carbon number that is 1 to 30, an alkoxy group having a carbon number that is 1 to 30, a halogen, a carboxyl group, a sulfone group, a nitro group, and a cyano group;

wherein X 2 and Y 2 may be individually the same or different, indicating a group selected from a direct bond, O, S, SO, SO 2 , CO, CH 2 , C(CH 3 ) 2 and C(CF 3 ) 2 , at least one of R 19 to R 30 is a hydroxyl group, and the others may be the same or different, indicating a group selected from a hydrogen atom, an alkyl group having a carbon number that is 1 to 30, an alkoxy group having a carbon number that is 1 to 30, a halogen, a carboxyl group, a sulfone group, a nitro group, and a cyano group;

wherein X 3 , Y 3 and Z 3 may be individually the same or different, indicating a group selected from a direct bond, O, S, SO, SO 2 , CO, CH 2 , C(CH 3 ) 2 and C(CF 3 ) 2 , at least one of R 31 to R 46 is a hydroxyl group, and the others may be the same or different, indicating a group selected from a hydrogen atom, an alkyl group having a carbon number that is 1 to 30, an alkoxy group having a carbon number that is 1 to 30, a halogen, a carboxyl group, a sulfone group, a nitro group, and a cyano group.

5. The resin composition according to claim 1 , wherein the aromatic diamine having an hydroxyl group is an aromatic diamine represented by any one of General formulas (2) to (5) below:

wherein at least one of R 7 to R 10 is a hydroxyl group, and the others may be the same or different, indicating a group selected from a hydrogen atom, an alkyl group having a carbon number that is 1 to 30, an alkoxy group having a carbon number that is 1 to 30, a halogen, a carboxyl group, a sulfone group, a nitro group, and a cyano group;

wherein X 1 indicates a group selected from a direct bond, O, S, SO, SO 2 , CO, CH 2 , C(CH 3 ) 2 and C(CF 3 ) 2 , at least one of R 11 to R 18 is a hydroxyl group, and the others may be the same or different, indicating a group selected from a hydrogen atom, an alkyl group having a carbon number that is 1 to 30, an alkoxy group having a carbon number that is 1 to 30, a halogen, a carboxyl group, a sulfone group, a nitro group, and a cyano group;

wherein X 2 and Y 2 may be individually the same or different, indicating a group selected from a direct bond, O, S, SO, SO 2 , CO, CH 2 , C(CH 3 ) 2 and C(CF 3 ) 2 , at least one of R 19 to R 30 is a hydroxyl group, and the others may be the same or different, indicating a group selected from a hydrogen atom, an alkyl group having a carbon number that is 1 to 30, an alkoxy group having a carbon number that is 1 to 30, a halogen, a carboxyl group, a sulfone group, a nitro group, and a cyano group;

wherein X 3 , Y 3 and Z 3 may be individually the same or different, indicating a group selected from a direct bond, O, S, SO, SO 2 , CO, CH 2 , C(CH 3 ) 2 and C(CF 3 ) 2 , at least one of R 31 to R 46 is a hydroxyl group, and the others may be the same or different, indicating a group selected from a hydrogen atom, an alkyl group having a carbon number that is 1 to 30, an alkoxy group having a carbon number that is 1 to 30, a halogen, a carboxyl group, a sulfone group, a nitro group, and a cyano group.

6. The resin composition according to claim 1 , wherein the methylol-based compound is a compound having two or more groups represented by general formula (6)
CH 2 —O—R 47 )  (6)

wherein R 47 , in the case where a plurality of R 47 exists in the compound, may be individually the same or different, indicating hydrogen or an alkyl group having a carbon number that is 1 to 10.

7. The resin composition according claim 1 , wherein a content of the methylol-based compound is 1 to 20 parts by weight relative to 100 parts by weight of the polyimide-based resin.

8. The resin composition according to claim 1 , wherein the acid dianhydride residue is a residue of an aromatic tetracarboxylic dianhydride.

9. A cured membrane obtained by curing the resin composition according to claim 1 .

10. A laminate film obtained by laminating the resin composition according to claim 1 on at least one surface of a heat resistant insulation film.

11. The laminate film according to claim 10 , wherein the surface of the heat resistant insulation film has been subjected to a mold release treatment.

12. The laminate film according to claim 10 , obtained by further laminating a heat resistant insulation film having been subjected to a mold release treatment on a surface of the resin composition having been laminated

Assignees

• Toray Industries

Inventors

• Watanabe Takuo
• Lee Chungseon

Classifications

• H10P72/7402

  Wafer tapes, e.g. grinding or dicing support tapes · CPC title

• H10P50/00

  Etching of wafers, substrates or parts of devices · CPC title

• C09J2203/326

  for bonding electronic components such as wafers, chips or semiconductors · CPC title

• C08G73/1042

  Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds · CPC title

• C09J183/10

  Block or graft copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09J151/08, C09J153/00) · CPC title