IP Library Granted Patent US 8,944,580
Granted Patent B2
US 8,944,580 · App. 13/510,609 · Granted Feb 3, 2015

Photosensitive resin composition, method for manufacturing structural body, and liquid discharge head

Inventors: Ken Ikegame (Atsugi, JP); Masako Shimomura (Yokohama, JP); Hyo Takahashi (Kawasaki, JP)
Assignee: Canon Kabushiki Kaisha
G03F7/0045C08G59/68C08G65/105C08G65/18G03F7/038C08L31/06G03F7/0046
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Quick Facts
Patent No.
US 8,944,580
App. No.
13/510,609
Granted
Feb 3, 2015
Kind
B2
Abstract

A photosensitive resin composition includes: a cation polymerizable compound; a photoacid generator having an anion portion represented by the chemical formula 1 and a cation portion, wherein R represents a hydrocarbon group which may be substituted with a fluorine atom and has a total carbon number of 1 to 30; X is selected from the group consisting of a carbon atom and a phosphorous atom; Y is selected from the group consisting of —S(═O) 2 —, —O—CF 2 —, —C(═O)—CF 2 —, —O—C(═O)—CF 2 —, —C(═O)—O—CF 2 —, and a single bond; R has at least one fluorine atom when Y is —S(═O) 2 — or the single bond; m and n are integers selected from the group consisting of m+n=3 and n=0, 1, and 2 when X is the carbon atom; m and n are integers selected from the group consisting of m+n=6 and n=0 to 5 when X is the phosphorous atom; and R and Y may be different from each other when m is equal to or greater than 2; and a salt of an anion portion and a cation portion, wherein an acid strength of an acid derived from the anion portion is equal to or greater than that of hexafluorophosphoric acid and equal to or less than that of hexafluoroantimonic acid.

Claims (30)

1. A photosensitive resin composition comprising:

a cation polymerizable compound; and

a photoacid generator having an anion portion represented by a chemical formula I and a cation represented by a chemical formula 4,

wherein R represents a hydrocarbon group which may be substituted with a fluorine atom and has a total carbon number of 1 to 30; X is selected from the group consisting of a carbon atom and a phosphorous atom; Y is selected from the group consisting of —S(═O) 2 —, —O—CF 2 —, —C(═O)—CF 2 —, —O—C(═O)—CF 2 —, —C(═O)—O—CF 2 —, and a single bond; R has at least one fluorine atom when Y is —S(═O) 2 — or the single bond; m and n are integers selected from the group consisting of m+n=3 and n=0, 1, and 2 when X is the carbon atom; m and n are integers selected from the group consisting of m+n=6 and n=0 to 5 when X is the phosphorous atom; and R and Y may be different from each other when m is equal to or greater than 2;

wherein R 1 to R 3 represent an aryl group having a total carbon number of 6 to 30, a heterocyclic group having a total carbon number of 4 to 30, an alkyl group having a total carbon number of 1 to 30, an alkenyl group having a total carbon number of 2 to 30, or an alkynyl group having a total carbon number of 2 to 30, R 1 to R 3 have at least two oxygen atoms included in the total component atoms; and

a salt of the anion portion and the cation portion, wherein an acid strength of an acid derived from the anion portion is equal to or less than that of hexafluoroantimonic acid.

2. The photosensitive resin composition according to claim 1 , wherein a molar number of the salt in the photosensitive resin composition is equal to or greater than three times that of the photoacid generator.

3. The photosensitive resin composition according to claim 1 , wherein the cation polymerizable compound has one of an epoxy group and an oxetane group.

4. The photosensitive resin composition according to claim 1 , wherein the cation polymerizable compound is a novolak epoxy resin.

5. The photosensitive resin composition according to claim 1 , wherein the cation polymerizable compound is a polyfunctional epoxy resin having an alicyclic skeleton.

6. The photosensitive resin composition according to claim 1 , wherein the anion portion of the photoacid generator has a structure represented by the following formula:

7. The photosensitive resin composition according to claim 1 , wherein the anion portion of the photoacid generator has a structure represented by the following formula:

8. A method for manufacturing a structural body comprising in this order:

preparing a substrate having the photosensitive resin composition of claim 1 provided thereon, the photosensitive resin composition constituting the structural body; exposing the photosensitive resin composition to cure an exposed portion thereof, thereby forming a cured product thereof, and removing an uncured portion; and

heating the cured product to 160° C. or higher.

9. A liquid discharge head comprising:

a discharge port member having a discharge port for discharging liquid,

wherein the discharge port member comprises a cured product of a resin composition,

the resin composition comprising:

a cation polymerizable compound;

a photoacid generator having an anion portion represented by a chemical formula 1 and a cation portion represented by a chemical formula 4,

wherein R represents a hydrocarbon group which may be substituted with a fluorine atom and has a total carbon number of 1 to 30; X is selected from the group consisting of a carbon atom and a phosphorous atom; Y is selected from the group consisting of —S(═O) 2 —, —O—CF 2 —, —C(═O)—CF 2 —, —O—C(═O)—CF 2 —, —C(═O)—O—CF 2 —, and a single bond; R has at least one fluorine atom when Y is —S(═O) 2 — or the single bond; m and n are integers selected from the group consisting of m+n=3 and n=0, 1, and 2 when X is the carbon atom; m and n are integers selected from the group consisting of m+n=6 and n=0 to 5 when X is the phosphorous atom; and R and Y may be different from each other when m is equal to or greater than 2;

wherein R 1 to R 3 represent an aryl group having a total carbon number of 6 to 30, a heterocyclic group having a total carbon number of 4 to 30, an alkyl group having a total carbon number of 1 to 30, an alkenyl group having a total carbon number of 2 to 30, or an alkynyl group having a total carbon number of 2 to 30, R 1 to R 3 have at least two oxygen atoms included in the total component atoms; and

a salt of the anion portion and the cation portion, wherein an acid strength of an acid derived from the anion portion is equal to or less than that of hexafluoroantimonic acid.

10. The liquid discharge head according to claim 9 , wherein a molar number of the salt in the photosensitive resin composition is equal to or greater than three times that of the photoacid generator.

11. The liquid discharge head according to claim 9 , wherein the cation polymerizable compound has one of an epoxy group and an oxetane group.

12. The liquid discharge head according to claim 9 , wherein the cation polymerizable compound is a novolak epoxy resin.

13. The liquid discharge head according to claim 9 , wherein the cation polymerizable compound is a polyfunctional epoxy resin having an alicyclic skeleton.

14. The liquid discharge head according to claim 9 , wherein the anion portion of the photoacid generator has a structure represented by the following formula:

15. The liquid discharge head according to claim 9 , wherein the anion portion of the photoacid generator has a structure represented by the following formula:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 21, 2012
From: IKEGAME, KEN; SHIMOMURA, MASAKO; TAKAHASHI, HYO
To: CANON KABUSHIKI KAISHA
Reel/Frame 028414/0486 →
Priority Claims (1)
JP 2010-024683 · Feb 5, 2010 · national
Continuity (1)
Related Publication 20120229556A1 · Sep 13, 2012