US 8,944,580 B2 · Photosensitive resin composition, method for manufacturing structural body, and liquid discharge head

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—CF2—, —C(═O)—CF2—, —O—C(═O)—CF2—, —C(═O)—O—CF2—, 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.

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Claims15

Dependent claims

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—CF2—, —C(═O)—CF2—, —O—C(═O)—CF2—, —C(═O)—O—CF2—, 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 R1 to R3 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, R1 to R3 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 more elements

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—CF2—, —C(═O)—CF2—, —O—C(═O)—CF2—, —C(═O)—O—CF2—, 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 R1 to R3 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, R1 to R3 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.

12 more elements

Dependencies are inferred from the claim text.

Description7,975 words

Summary801 words

#The present invention relates to a negative photosensitive resin composition. Specifically, the present invention relates to a negative photosensitive resin composition which is suitable and can be used for manufacturing a liquid discharge head for generating droplets such as ink small droplets used for a liquid discharge recording system. The present invention relates to a liquid discharge head using the negative photosensitive resin composition.

#A photolithography technique has been heretofore known as one of microfabrication techniques. In the photolithography technique, a negative photosensitive resin is exposed and developed to form a pattern and a structure. This technique is widely used in manufacture applications such as a semiconductor integrated circuit, a semiconductor exposing mask, and various MEMS (Micro ElectroMechanical Systems). The technique is applied to manufacture a nozzle of a liquid discharge head, as an example of the manufacture applications of the MEMS. For example, a stepper having an i-line as a light source is widely used as an exposing device. In this technical field, recently, manufacture of a more complex and high-definition structure object has been required. Therefore, a negative photosensitive resin composition exhibiting high photosensitivity and molding accuracy to light from a light source has been required.

#Japanese Patent Application Laid-Open No. 2008-256980 discloses a photosensitive resin composition containing a polyfunctional epoxy resin and a photoacid generator, as an example of the negative photosensitive resin compositions. An acid derived from an anion portion structure of the photoacid generator used herein has a strong acid strength, and improve sensitivity of the photosensitive resin composition compared with hexafluoroantimonic acid.

Brief description of the drawings6 figures

#FIG. 1 is a schematic view of a pattern used in order to evaluate molding accuracy in an embodiment of the present invention.

#FIG. 2 is a schematic perspective view of a liquid discharge head in the embodiment of the present invention.

#FIG. 3 is a schematic perspective view of a substrate used for the liquid discharge head in the embodiment of the present invention.

Detailed description7,017 words

#Each of components of a photosensitive resin composition according to the present invention will be described in detail.

#<Acid-Polymerizable Compound>

#An acid-polymerizable compound is not particularly limited but may be, for example, a compound having one or more reactive functional groups selected from the group consisting of an epoxy group, an oxetane group, a vinyl ether group, and a propenyl ether group.

Facts

Application

13/510,609Filed 31 Jan 2011

Priority

JP 2010-0246835 Feb 2010

Published

US 2012/0229556 A113 Sep 2012

Granted

3 Feb 2015

Term ends

24 Feb 2032

Estimated · how

20 years from earliest known nonprovisional domestic filing plus recorded patent term adjustment, including 389 days of adjustment. Maintenance-fee lapses, terminal disclaimers and statutory extensions have not been checked. The continuity chain may be incomplete; this is not an enforceability determination.

Classification10 codes

G03F 7/0045
Photosensitive materials: with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
C08G 59/68
Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react…:…
C08G 65/105
Characterised by the catalysts used: onium compounds
C08G 65/18
Cyclic ethers having four or more ring atoms: oxetanes

Timeline

5 Feb 2010Priority claimedJP 2010-024683
31 Jan 2011Application filedUS 13/510,609
21 Jun 2012Assigned to Canon Kabushiki Kaishaassignment of assignor's interest
13 Sep 2012PublishedUS 2012/0229556 A1
3 Feb 2015GrantedUS 8,944,580 B2
12 Oct 2026TodayWithin its term
24 Feb 2032Term endsEstimated, includes 389 days of adjustment

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

Life of this patent

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

Life of this patent

Life of this patent

Abstract

Drawings

Drawings

Claims15

Description7,975 words

Drawings

Classification10 codes

Life of this patent

Description7,975 words