Photosensitive resin composition, dry film resist, and cured objects obtained therefrom

Patent metadata

Field	Value
Publication number	US-11809078-B2
Application number	US-201816769361-A
Country	US
Kind code	B2
Filing date	Nov 29, 2018
Priority date	Dec 6, 2017
Publication date	Nov 7, 2023
Grant date	Nov 7, 2023

Abstract

A purpose of the present invention is to provide a photosensitive resin composition which retains satisfactory image resolution and gives cured objects reduced in wet-heat dissolution or contamination and having satisfactory wet-heat adhesiveness. The photosensitive resin composition of the present invention comprises: (A) a cationic photopolymerization initiator which comprises a salt of a cation with an anion represented by formula (1) (wherein R 1 to R 4 each independently represent a C1 −18 alkyl or C 6-14 aryl group, provided that at least one of R 1 to R 4 represents a C 6-14 aryl group); and (B) an epoxy compound. R 1 to R 4 may be each independently either a phenyl group having one or more perfluoroalkyl groups as substituents or a phenyl group having one or more fluorine atoms as substituents. R 1 to R 4 may be each independently a pentafluorophenyl or bis(trifluoromethyl)phenyl group.

First claim

The invention claimed is:

1. A photosensitive resin composition comprising a cationic photopolymerization initiator (A) and an epoxy compound (B), wherein:
the cationic photopolymerization initiator (A) comprises a salt composed of an anion represented by a following formula (1) and a cation,

wherein R 1 to R 4 each independently denotes an alkyl group having 1 to 18 carbon atom(s) or an aryl group having 6 to 14 carbon atoms, and at least one of R 1 to R 4 denotes the aryl group having 6 to 14 carbon atoms; and
the epoxy resin (B) includes an epoxy compound (b-2) represented by a following formula (3),

wherein R 6 each independently denotes an alkyl group having 2 to 4 carbon atom(s), or a trifluoromethyl group, R 7 denotes a hydrogen atom, and m is an average repetition number and denotes a real number in a range of from 1 to 30; and/or
an epoxy compound (b-9) represented by a following formula (15),

wherein R 13 each independently denotes a hydrogen atom or an alkyl group having 1 to 4 carbon atom(s), and s is an average repetition number and denotes a real number in a range of from 0 to 30; and
the epoxy resin (B) optionally includes one or two or more kinds of epoxy compounds selected from a group consisting of:
an epoxy compound (b-3) represented by a following formula (4),

wherein R 8 each independently denotes a hydrogen atom or an alkyl group having 1 to 4 carbon atom(s), and n is an average repetition number and denotes a real number in a range of from 0 to 30;
one or more kinds of epoxy compounds (b-4) selected from a group consisting of epoxy compounds represented by following formulae (5) to (7),

wherein, in the formula (6), R 9 each independently denotes a hydrogen atom or a glycidyl group, and, in the formula (7), R 10 each independently denotes a hydrogen atom or a glycidyl group;
an epoxy compound (b-5) that is a co-condensation product of a compound represented by following formula (8) and/or formula (9), and a compound represented by following formula (10) and/or formula (11);

an epoxy compound (b-6) represented by a following formula (12)

wherein R 12 each independently denotes an alkyl group having 2 to 4 carbon atom(s), and p is an average repetition number and denotes a real number in a range of from 0 to 10;
an epoxy compound (b-7) represented by a following formula (13),

wherein q is an average repetition number and denotes a real number in a range of from 0 to 5;
and
an epoxy compound (b-10) represented by a following formula (16),

wherein t, u and v each is an average repetition number and denotes a real number satisfying a relation of 2≤t+u+v≤60.

2. The photosensitive resin composition according to claim 1 , wherein R 1 to R 4 each independently denotes a phenyl group having a perfluoroalkyl group as a substituent or a phenyl group having a fluorine atom as a substituent.

3. The photosensitive resin composition according to claim 2 , wherein R 1 to R 4 each independently denotes a pentafluorophenyl group or a bis(trifluoromethyl)phenyl group.

4. The photosensitive resin composition according to claim 1 , wherein the cationic photopolymerization initiator (A) comprises the salt composed of the anion represented by the formula (1) and the cation having an iodine atom or a sulfur atom.

5. A dry film resist comprising the photosensitive resin composition according to claim 1 between substrates.

6. A cured product of the photosensitive resin composition according to claim 1 .

7. The photosensitive resin composition according to claim 2 , wherein the cationic photopolymerization initiator (A) comprises the salt composed of the anion represented by the formula (1) and the cation having an iodine atom or a sulfur atom.

8. The photosensitive resin composition according to claim 3 , wherein the cationic photopolymerization initiator (A) comprises the salt composed of the anion represented by the formula (1) and the cation having an iodine atom or a sulfur atom.

9. A dry film resist comprising the photosensitive resin composition according to claim 2 between substrates.

10. A dry film resist comprising the photosensitive resin composition according to claim 3 between substrates.

11. A dry film resist comprising the photosensitive resin composition according to claim 4 between substrates.

12. A dry film resist comprising the photosensitive resin composition according to claim 7 between substrates.

13. A dry film resist comprising the photosensitive resin composition according to claim 8 between substrates.

14. A cured product of the photosensitive resin composition according to claim 2 .

15. A cured product of the photosensitive resin composition according to claim 3 .

16. A cured product of the photosensitive resin composition according to claim 4 .

17. A cured product of the photosensitive resin composition according to claim 7 .

18. A cured product of the photosensitive resin composition according to claim 8 .

19. A cured product of the dry film resist according to claim 5 .

20. A cured product of the dry film resist according to claim 9 .

21. A cured product of the dry film resist according to claim 10 .

22. A cured product of the dry film resist according to claim 11 .

23. A cured product of the dry film resist according to claim 12 .

24. A cured product of the dry film resist according to claim 13 .

25. A photosensitive resin composition comprising a cationic photopolymerization initiator (A) and an epoxy compound (B), wherein:
the cationic photopolymerization initiator (A) comprises a salt composed of an anion represented by a following formula (1) and a cation,

wherein R 1 to R 4 each independently denotes an alkyl group having 1 to 18 carbon atom(s) or an aryl group having 6 to 14 carbon atoms, and at least one of R 1 to R 4 denotes the aryl group having 6 to 14 carbon atoms; and
the epoxy resin (B) includes an epoxy compound (b-9)

Assignees

• Nipppon Kayaku Kk
• Nippon Kayaku Kk

Inventors

• Imaizumi Naoko

Classifications

• G03F7/038 Primary

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

• B32B15/043

  of metal (B32B15/01 takes precedence) · CPC title

• B32B15/20

  comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)} · CPC title

• B32B17/06 Primary

  comprising glass as the main or only constituent of a layer, next to another layer of a specific {material} · CPC title

• B32B18/00

  Layered products essentially comprising ceramics, e.g. refractory products · CPC title