Photosensitive resin composition, photosensitive resin coating, photosensitive dry film, pattern formation method

Patent metadata

Field	Value
Publication number	US-12448485-B2
Application number	US-202117792210-A
Country	US
Kind code	B2
Filing date	Jan 13, 2021
Priority date	Jan 24, 2020
Publication date	Oct 21, 2025
Grant date	Oct 21, 2025

Abstract

Provided is a photosensitive resin composition that includes: a silicone resin (A) having an epoxy group and/or a phenolic hydroxyl group; an alkyl phenol novolac resin (B) indicated by formula (B); and a photoacid generator (C).

(In the formula, R 51 is a C1-9 saturated hydrocarbyl group. R 52 is a C10-25 saturated hydrocarbyl group. n 1 and n 2 are numbers that fulfil 0≤n 1 <1, 0<n 2 ≤1, and n 1 +n 2 =1. m 1 represents an integer from 0 to 3 and m 2 represents an integer from 1 to 3.)

First claim

The invention claimed is:

1. A photosensitive resin composition comprising
(A) a silicone resin containing an epoxy group and/or phenolic hydroxy group, the silicone resin having the formula (A):

wherein R 1 to R 4 are each independently a C 1 -C 8 monovalent hydrocarbon group, k is an integer of 1 to 600, a and b are numbers in the range: 0<a<1, 0<b<1, and a+b=1, and X is a divalent organic group containing an epoxy group and/or phenolic hydroxy group,
(B) an alkyl phenol novolak resin having the formula (B):

wherein R 51 is a C 1 -C 9 saturated hydrocarbyl group, R 52 is a C 10 -C 25 saturated hydrocarbyl group, n 1 and n 2 are numbers in the range: 0≤n 1 <1, 0<n 2 ≤1, and n 1 +n 2 =1, m 1 is an integer of 0 to 3, and m 2 is an integer of 1 to 3, and
(C) a photoacid generator.

2. The photosensitive resin composition of claim 1 wherein the silicone resin (A) comprises repeat units having the formulae (a1) to (a4) and (b1) to (b4):

wherein R 1 to R 4 are each independently a C 1 -C 8 monovalent hydrocarbon group, k is an integer of 1 to 600, a 1 to a 4 and b 1 to b 4 are numbers in the range: 0≤a 1 <1, 0≤a 2 <1, 0≤a 3 <1, 0≤a 4 <1, 0≤b 1 <1, 0≤b 2 <1, 0≤b 3 <1, 0≤b 4 <1, 0<a 1 +a 2 +a 3 <1, 0<b 1 +b 2 +b 3 <1, a 1 +a 2 +a 3 +a 4 +b 1 +b 2 +b 3 +b 4=1 , X 1 is a divalent group having the following formula (X 1 ), X 2 is a divalent group having the following formula (X2), X 3 is a divalent group having the following formula (X3), X 4 is a divalent group having the following formula (X4),

wherein Y 1 is a single bond, methylene, propane-2,2-diyl, 1,1,1,3,3,3-hexafluoropropane-2,2-diyl or fluorene-9,9-diyl, R 11 and R 12 are each independently hydrogen or methyl, R 13 and R 14 are each independently a C 1 -C 4 saturated hydrocarbyl or C 1 -C 4 saturated hydrocarbyloxy group, p 1 and p 2 are each independently an integer of 0 to 7, q 1 and q 2 are each independently an integer of 0 to 2, the broken line designates a valence bond,

wherein Y 2 is a single bond, methylene, propane-2,2-diyl, 1,1,1,3,3,3-hexafluoropropane-2,2-diyl or fluorene-9,9-diyl, R 21 and R 22 are each independently hydrogen or methyl, R 23 and R 24 are each independently a C 1 -C 4 saturated hydrocarbyl or C 1 -C 4 saturated hydrocarbyloxy group, r 1 and r 2 are each independently an integer of 0 to 7, s 1 and s 2 are each independently an integer of 0 to 2, the broken line designates a valence bond,

wherein R 31 and R 32 are each independently hydrogen or methyl, t 1 and t 2 are each independently an integer of 0 to 7, the broken line designates a valence bond,

wherein R 41 and R 42 are each independently hydrogen or methyl, R 43 and R 44 are each independently a C 1 -C 8 hydrocarbyl group, u 1 and u 2 are each independently an integer of 0 to 7, v is an integer of 0 to 600, and the broken line designates a valence bond.

3. The photosensitive resin composition of claim 1 wherein the amount of the alkyl phenol novolak resin as component (B) is 3 to 100 parts by weight per 100 parts by weight of component (A).

4. The photosensitive resin composition of claim 1 , further comprising (D) a crosslinker.

5. The photosensitive resin composition of claim 4 wherein the crosslinker (D) is at least one compound selected from a nitrogen-containing compound selected from melamine, guanamine, glycoluril and urea compounds, having on the average at least two methylol and/or alkoxymethyl groups in the molecule, an amino condensate modified with formaldehyde or formaldehyde-alcohol, a phenol compound having on the average at least two methylol or alkoxymethyl groups in the molecule, and an epoxy compound having on the average at least two epoxy groups in the molecule.

6. The photosensitive resin composition of claim 1 , further comprising (E) a solvent.

7. The photosensitive resin composition of claim 1 which is capable of use as a coating for protecting electric and electronic parts.

8. The photosensitive resin composition of claim 1 which is capable of use as a substrate-bonding coating for bonding two substrates.

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

10. A photosensitive dry film comprising a support and the photosensitive resin coating of claim 9 thereon.

11. A pattern forming process comprising the steps of:
(i) applying the photosensitive resin composition of claim 1 onto a substrate to form a photosensitive resin coating thereon,
(ii) exposing the photosensitive resin coating to radiation, and
(iii) developing the exposed resin coating in a developer to form a pattern of the resin coating.

12. The pattern forming process of claim 11 , further comprising (iv) post-curing the patterned resin coating resulting from the development step at a temperature of 100 to 250° C.

13. A pattern forming process comprising the steps of:
(i′) attaching the photosensitive resin coating of the photosensitive dry film of claim 10 to a substrate to form the photosensitive resin coating on the substrate,
(ii) exposing the photosensitive resin coating to radiation, and
(iii) developing the exposed resin coating in a developer to form a pattern of the resin coating.

Assignees

• Shinetsu Chemical Co

Inventors

• Maruyama Hitoshi

Classifications

• H10P14/6922

  the material containing Si, O and at least one of H, N, C, F or other non-metal elements, e.g. SiOC, SiOC:H or SiONC · CPC title

• H10P14/6686

  the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane · CPC title

• G03F7/0757 Primary

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

• C08L63/04

  Epoxynovolacs · CPC title

• C08G77/52

  containing aromatic rings · CPC title