Siloxane polymer containing isocyanuric acid and polyether skeletons, photosensitive resin composition, pattern forming process, and fabrication of opto-semiconductor device

Patent metadata

Field	Value
Publication number	US-11548985-B2
Application number	US-201916676591-A
Country	US
Kind code	B2
Filing date	Nov 7, 2019
Priority date	Nov 28, 2018
Publication date	Jan 10, 2023
Grant date	Jan 10, 2023

Abstract

A siloxane polymer comprising polysiloxane, silphenylene, isocyanuric acid, and polyether skeletons in a backbone and having an epoxy group in a side chain is provided. A photosensitive resin composition comprising the siloxane polymer and a photoacid generator is coated to form a film which can be patterned using radiation of widely varying wavelength. The patterned film has high transparency and light resistance.

First claim

The invention claimed is:

1. A siloxane polymer comprising a polysiloxane skeleton, silphenylene skeleton, isocyanuric acid skeleton, and polyether skeleton in a backbone and having an epoxy group in a side chain,
wherein the polymer comprises repeating units having the following formulae (A1) to (A4):

wherein R 1 to R 4 are each independently a C 1 -C 20 monovalent hydrocarbon group which may contain a heteroatom, m is each independently an integer of 1 to 600, with the proviso that when m is an integer of at least 2, groups R 3 may be identical or different and groups R 4 may be identical or different, a 1 , a 2 , a 3 , and a 4 are numbers in the range: 0<a 1 <1, 0<a 2 <1, 0<a 3 <1, 0<a 4 <1, and a 1 +a 2 +a 3 +a 4 =1,
X 1 is a divalent group having the formula (X1):

wherein R 11 and R 12 are each independently hydrogen or methyl, n 1 and n 2 are each independently an integer of 0 to 7, R 13 is a C 1 -C 8 divalent hydrocarbon group in which an ester bond or ether bond may intervene between carbon atoms, and
X 2 is a divalent group having the formula (X2):

wherein R 21 and R 22 are each independently hydrogen or a C 1 -C 8 monovalent hydrocarbon group, R 23 and R 24 are each independently hydrogen or methyl, p 1 and p 2 are each independently an integer of 1 to 6, and q is an integer of 0 to 100.

2. The polymer of claim 1 wherein a film of the polymer having a thickness of 10 μm has a transmittance of at least 97% with respect to light of wavelength 405 nm.

3. The polymer of claim 1 wherein q is an integer of 5 to 20.

4. The polymer of claim 1 wherein m is an integer of 10 to 100.

5. The polymer of claim 1 wherein R 11 , R 12 , R 21 and R 22 are hydrogen.

6. The polymer of claim 1 , having a weight average molecular weight of 3,000 to 500,000.

7. A photosensitive resin composition comprising (A) the siloxane polymer of claim 1 and (B) a photoacid generator.

8. The photosensitive resin composition of claim 7 wherein component (B) is present in an amount of 0.05 to 20 parts by weight per 100 parts by weight of component (A).

9. The photosensitive resin composition of claim 7 , further comprising (C) a cationic polymerizable crosslinker.

10. The photosensitive resin composition of claim 7 , further comprising (D) a solvent.

11. The photosensitive resin composition of claim 7 , further comprising (E) an antioxidant.

12. A pattern forming process comprising the steps of:
(i) applying the photosensitive resin composition of claim 7 onto a substrate to form a photosensitive resin film thereon,
(ii) exposing the photosensitive resin film to radiation, and
(iii) developing the exposed resin film in a developer.

13. A method for fabricating an opto-semiconductor device involving the pattern forming process of claim 12 , the device comprising the patterned photosensitive resin film.

14. The polymer of claim 1 wherein the polyether skeleton is represented by the formula (X2):

wherein R 21 and R 22 are each independently hydrogen or a C 1 -C 8 monovalent hydrocarbon group, R 23 and R 24 are each independently hydrogen or methyl, p 1 and p 2 are each independently an integer of 1 to 6, and q is an integer of 0 to 100.

Assignees

• Shinetsu Chemical Co

Inventors

• Maruyama Hitoshi
• Soga Kyoko

Classifications

• G03F7/20

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

• C08G77/52 Primary

  containing aromatic rings · CPC title

• G03F7/38

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

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• C09D183/12

  containing polyether sequences · CPC title