Photosensitive resin composition, dry film using same, printed wiring board, and printed wiring board manufacturing method

Patent metadata

Field	Value
Publication number	US-12189290-B2
Application number	US-202318220308-A
Country	US
Kind code	B2
Filing date	Jul 11, 2023
Priority date	Mar 30, 2017
Publication date	Jan 7, 2025
Grant date	Jan 7, 2025

Abstract

There are provided a photosensitive resin composition which can be applied to either a projection exposure or direct-write exposure machine without fine adjustment of the composition, and can form a resist pattern having an excellent cross-sectional shape in which an undercut in which the bottom portion of the resist pattern is hollowed and omission of the top of the resist pattern are less likely to occur, and a line width of an intermediate portion (central portion) and a deepest portion (bottom portion) in the depth direction of the cross section of the resist pattern is less likely to be larger than a line width of the surface portion (that is, linearity in the depth direction of the resist pattern contour is favorable), and which has excellent insulation reliability and crack resistance reliability, and a dry film using the same, a printed wiring board, and a printed wiring board manufacturing method. The photosensitive resin composition includes an acid-modified vinyl group-containing epoxy resin (A), a photopolymerization initiator (B), a photopolymerization sensitizer including a benzophenone compound (C), and a photopolymerizable compound (D).

First claim

The invention claimed is:

1. A photosensitive resin composition comprising:
an acid-modified vinyl group-containing epoxy resin (A);
a photopolymerization initiator (B);
a photopolymerization sensitizer containing a benzophenone compound (C); and
a photopolymerizable compound (D), wherein
a content of the component (A) is in a range of 20 to 80 mass % with respect to a total solid content of the photosensitive resin composition,
the photopolymerization initiator (B) is at least one selected from the group consisting of an alkylphenone photopolymerization initiator, an acylphosphine oxide photopolymerization initiator, a titanocene photopolymerization initiator, and an oxime ester photopolymerization initiator, and
the benzophenone compound contained in the component (C) is a benzophenone compound having at least one group selected from the group consisting of an amino group, an ethylamino group, a dimethylamino group, a diethylamino group, a dibutylamino group, a hydroxyl group, a methoxy group, an ethoxy group, a butoxy group, and a phenyl group.

2. The photosensitive resin composition according to claim 1 , wherein the component (A) includes at least one acid-modified vinyl group-containing epoxy resin (A1) synthesized using a bisphenol novolak type epoxy resin (a1).

3. The photosensitive resin composition according to claim 2 , wherein the acid-modified vinyl group-containing epoxy resin (A1) is a resin obtained by reacting a resin (A1′) obtained by reacting the epoxy resin (a1) with a vinyl group-containing monocarboxylic acid (b) with a saturated or unsaturated group-containing polybasic acid anhydride (c).

4. The photosensitive resin composition according to claim 2 , wherein the bisphenol novolak type epoxy resin (a1) is at least one selected from the group consisting of bisphenol novolak type epoxy resins having a structural unit represented by the following General Formula (I) and bisphenol novolak type epoxy resins having a structural unit represented by the following General Formula (II):

[in General Formula (I), R 11 represents a hydrogen atom or a methyl group, Y 1 and Y 2 each independently represent a hydrogen atom or a glycidyl group, a plurality of R 11 's may be the same as or different from each other, and at least one of Y 1 and Y 2 represents a glycidyl group]

[in General Formula (II), R 12 represents a hydrogen atom or a methyl group, Y 3 and Y 4 each independently represent a hydrogen atom or a glycidyl group, a plurality of R 12 's may be the same as or different from each other, and at least one of Y 3 and Y 4 represents a glycidyl group].

5. The photosensitive resin composition according to claim 1 , wherein the component (A) includes at least one acid-modified vinyl group-containing epoxy resin (A2) synthesized using an epoxy resin (a2) different from a bisphenol novolak type epoxy resin.

6. The photosensitive resin composition according to claim 5 , wherein the epoxy resin (a2) is at least one selected from the group consisting of a novolak type epoxy resin, a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, and a triphenolmethane type epoxy resin.

7. The photosensitive resin composition according to claim 5 , wherein the acid-modified vinyl group-containing epoxy resin (A2) is a resin obtained by reacting a resin (A2′) obtained by reacting the epoxy resin (a2) with a vinyl group-containing monocarboxylic acid (b) with a saturated or unsaturated group-containing polybasic acid anhydride (c).

8. The photosensitive resin composition according to claim 5 , wherein the epoxy resin (a2) is at least one selected from the group consisting of a novolak type epoxy resin having a structural unit represented by the following General Formula (III), a bisphenol type epoxy resin having a structural unit represented by the following General Formula (IV), and a triphenolmethane type epoxy resin having a structural unit represented by the following General Formula (V):

[in General Formula (III), R 13 represents a hydrogen atom or a methyl group, Y 5 represents a hydrogen atom or a glycidyl group, and a molar ratio between hydrogen atoms and glycidyl groups (hydrogen atoms/glycidyl groups) is 0/100 to 30/70]

[in General Formula (IV), R 14 represents a hydrogen atom or a methyl group, Y 6 represents a hydrogen atom or a glycidyl group, a molar ratio between hydrogen atoms and glycidyl groups (hydrogen atoms/glycidyl groups) is 0/100 to 30/70, and a plurality of R 14 's may be the same as or different from each other]

[in General Formula (V), Y 7 represents a hydrogen atom or a glycidyl group, a plurality of Y 7 's may be the same as or different from each other, and at least one Y 7 is a glycidyl group].

9. The photosensitive resin composition according to claim 8 , wherein the epoxy resin (a2) is a novolak type epoxy resin having a structural unit represented by General Formula (III).

10. The photosensitive resin composition according to claim 1 , wherein the photopolymerization initiator (B) is at least one selected from the group consisting of an alkylphenone photopolymerization initiator, an acylphosphine oxide photopolymerization initiator, and an oxime ester photopolymerization initiator.

11. The photosensitive resin composition according to claim 1 , wherein the photopolymerization initiator (B) is an acylphosphine oxide photopolymerization initiator.

12. The photosensitive resin composition according to claim 1 , further comprising a pigment (E).

13. The photosensitive resin composition according to claim 1 , further comprising an inorganic filler (F).

14. A dry film comprising:
a carrier film; and
a photosensitive layer using the photosensitive resin composition according to claim 1 .

15. A printed wiring board comprising a permanent mask resist formed of the photosensitive resin composition according to claim 1 .

16. The printed wiring board according to claim 15 , wherein the thickness of the permanent mask resist is 10 μm or more.

17. A printed wiring board manufacturing method, comprising:
a process of providing a photosensitive layer on a substrate using the photosensitive resin composition according to claim 1 ;
a process of forming a resist pattern using the photosensitive layer; and
a process of curing the resist pattern to form a permanent mask resist, in this order.

18. A printed wiring board manufacturing method, comprising:
a process of providing a photosensitive layer on a substrate using the dry film according to claim 14 ;
a process of forming a resist pattern using the photosensitive layer; and
a process of curing the resist pattern to form a permanent mask resist, in this order.

Assignees

• Resonac Corp

Inventors

• Komuro Nobuhito
• Daijima Yuta
• Kojima Masayuki
• IRIZAWA Shinji
• Oosaki Shinya

Classifications

• G03F7/0385

  using epoxidised novolak resin · CPC title

• G03F7/40

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

• G03F7/032

  with binders · CPC title

• H05K3/0076

  characterised by the composition of the mask · CPC title

• G03F7/0382

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title