Photosensitive resin composition, photosensitive dry film, and pattern forming process

Patent metadata

Field	Value
Publication number	US-11460774-B2
Application number	US-201916716821-A
Country	US
Kind code	B2
Filing date	Dec 17, 2019
Priority date	Dec 19, 2018
Publication date	Oct 4, 2022
Grant date	Oct 4, 2022

Abstract

A photosensitive resin composition comprising a polymer containing a silphenylene skeleton and a fluorene skeleton and having a crosslinkable site in the molecule, a phenol compound having a Mw of 300-10,000, a photoacid generator, and a benzotriazole or imidazole compound has improved film properties. Even from a thick film, a fine size pattern can be formed.

First claim

The invention claimed is:

1. A photosensitive resin composition comprising
(A) a polymer comprising repeating units having the formula (A1) and repeating units of at least one type selected from repeating units having the formula (A2) and repeating units having the formula (A3), shown below,
(B) a phenol compound having a weight average molecular weight of 300 to 10,000,
(C) a photoacid generator,
(D) a benzotriazole compound and/or imidazole compound, and
(E) an organic solvent,

wherein X 1 and X 2 are each independently hydrogen or glycidyl group, Y 1 is a C 1 -C 5 straight or branched alkanediyl group, Z 1 is a C 1 -C 10 straight alkanediyl group which may contain hydroxyl, a C 2 -C 10 branched alkanediyl group, or a divalent group having the formula (A4):

wherein Z 11 and Z 13 are each independently a C 1 -C 5 straight or branched alkanediyl group, Z 12 is a C 1 -C 30 divalent hydrocarbon group, a 4 and a 5 are each independently an integer of 1 to 50, R 1 , R 2 , R 3 and R 4 are each independently hydrogen or a C 1 -C 10 monovalent hydrocarbon group, a 1 , a 2 and a 3 are numbers in the range: 0<a 1 <1,0≤a 2 <1,0 ≤a 3 <1, and a 1 +a 2 +a 3 =1, x and y are each independently an integer of 1 to 50.

2. A photosensitive resin coating obtained from the photosensitive resin composition of claim 1 .

3. A photosensitive dry film comprising a support film and the photosensitive resin coating of claim 2 thereon.

4. A pattern forming process comprising the steps of:
(a) applying the photosensitive resin composition of claim 1 onto a substrate to form a photosensitive resin coating thereon,
(b) exposing the photosensitive resin coating to radiation, and
(c) developing the exposed resin coating in an organic solvent.

5. A pattern forming process comprising the steps of:
(a′) using the photosensitive dry film of claim 3 to form the photosensitive resin coating on a substrate,
(b) exposing the photosensitive resin coating to radiation, and
(c) developing the exposed resin coating in an organic solvent.

6. The photosensitive resin composition of claim 1 wherein the phenol compound having a weight average molecular weight of 300 to 10,000 is selected from a novolak resin, polyhydroxystyrene, bisphenols, trisphenols, polyphenols, and compounds having the following formulae (B1), (B2) and (B3):

wherein j is 1 or 2; m, p and r are each independently an integer of 0 to 3, q is an integer of 1 to 3, and n is an integer of 1 to 4, meeting 1 ≤m+n+p ≤6, and 1 ≤q+r ≤5,
k is an integer of 2 or 3, q and r are as defined above,
s and t are each independently an integer of 0 to 3, meeting 0 ≤s+t 4,
R 11 to R 16 are each independently hydrogen, methyl, or a group having the formula (B4) below, with the proviso that at least one of R 11 to R 13 and at least one of R 14 to R 16 are a group having formula (B4) wherein u is an integer of 1 to 3,

wherein u and v are each independently an integer of 0 to 3, meeting 0 ≤u+v≤4.

Assignees

• Shinetsu Chemical Co

Inventors

• Hirano Yoshinori
• Sugo Michihiro
• Asai Satoshi
• Goi Takahiro

Classifications

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/0757 Primary

  Macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence) · CPC title

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• G03F7/0048

  characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents · CPC title

• G03F7/11

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title