Photosensitive resin composition, photosensitive resin laminate, and pattern forming process

Patent metadata

Field	Value
Publication number	US-11294283-B2
Application number	US-201916299702-A
Country	US
Kind code	B2
Filing date	Mar 12, 2019
Priority date	Mar 23, 2018
Publication date	Apr 5, 2022
Grant date	Apr 5, 2022

Abstract

A photosensitive resin composition is provided comprising 100 pbw of a polyimide silicone containing a primary alcoholic hydroxyl group, a crosslinker, a photoacid generator, a polyfunctional epoxy compound, 1-70 pbw of a filler having an average particle size of 0.01-20.0 μm, and 0.01-30 pbw of a colorant. The resin composition is colored and photosensitive and cures into a product having an improved modulus.

First claim

The invention claimed is:

1. A photosensitive resin composition comprising:
(A) a polyimide silicone containing 1.0×10 −7 to 8.0×10 −3 eq/g of primary alcoholic hydroxyl group,
(B) a crosslinker,
(C) a photoacid generator,
(D) a polyfunctional epoxy compound,
(E) a filler having an average particle size of 0.01 to 20.0 μm, in an amount of 1 to 70 parts by weight per 100 parts by weight of the polyimide silicone (A), and
(F) a colorant in an amount of 0.01 to 30 parts by weight per 100 parts by weight of the polyimide silicone (A), wherein the colorant (F) is carbon black.

2. The composition of claim 1 , further comprising (G) an organic solvent.

3. The composition of claim 1 wherein the organic solvent is at least one solvent selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, cyclohexanone, cyclopentanone, methyl isobutyl ketone, and γ-butyrolactone.

4. The composition of claim 1 wherein the polyimide silicone (A) comprises recurring units having the formula (1-1) and recurring units having the formula (1-2):

wherein X 1 is a tetravalent group having the formula (2):

wherein R 1 to R 6 are each independently a C 1 -C 8 monovalent hydrocarbon group, R 7 and R 8 are each independently a single bond or C 1 -C 12 divalent hydrocarbon group, R 9 and R 10 are each independently a trivalent organic group, m is an integer of 0 to 120, the broken line denotes a valence bond,
Y 1 is a group having the formula (3):

wherein A 1 to A 3 are each independently a single bond, methylene group, ether bond, sulfonyl group, amide bond, propane-2,2-diyl, 1,1,1,3,3,3-hexafluoropropane-2,2-diyl, or fluorene-9,9-diyl group, R 11 and R 12 are each independently a hydroxyl group or alcoholic hydroxyl-containing organic group, at least one of R 11 and R 12 being a primary alcoholic hydroxyl-containing organic group, R 13 to R 16 are each independently a C 1 -C 4 alkyl group, a is an integer of 0 to 10, b and c are each independently 0 or 1, d to g are each independently 0, 1 or 2,
X 2 is a tetravalent organic group other than the group of formula (2),
p and q are positive integers, meeting 0.01≤p/(p+q)<1, the broken line denotes a valence bond.

5. The composition of claim 4 wherein X 2 is a group selected from the following:

wherein the broken line denotes a valence bond.

6. The composition of claim 1 wherein component (D) comprises at least one compound selected from the group consisting of a bisphenol skeleton-bearing polyfunctional epoxy compound, phenol novolak polyfunctional epoxy compound, and polyfunctional epoxy silicone.

7. A photosensitive resin laminate comprising a support film layer, a photosensitive resin layer composed of the photosensitive resin composition of claim 1 , and a cover film layer.

8. A pattern forming process comprising the steps of:
(i) forming a photosensitive resin film on a substrate using the photosensitive resin composition of claim 1 ,
(ii) exposing the resin film to radiation, and
(iii) developing the resin film in a developer.

9. A pattern forming process comprising the steps of:
(i) forming a photosensitive resin film on a substrate using the photosensitive resin laminate of claim 7 ,
(ii) exposing the resin film to radiation, and
(iii) developing the resin film in a developer.

Assignees

• Shinetsu Chemical Co

Inventors

• ICHIOKA Yoichiro

Classifications

• G03F7/09

  characterised by structural details, e.g. supports, auxiliary layers (supports for printing plates in general B41N) · CPC title

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title

• G03F7/0048

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

• G03F7/0387 Primary

  Polyamides or polyimides · CPC title

• G03F7/0757 Primary

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