Acid- and radical-generating agent and method for generating acid and radical

Patent metadata

Field	Value
Publication number	US-10451967-B2
Application number	US-201415038955-A
Country	US
Kind code	B2
Filing date	Nov 21, 2014
Priority date	Nov 25, 2013
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

It is a subject of the present invention to provide an acid- and radical-generating agent which has high sensitivity to an active energy ray having a wavelength of around 300 to 450 nm, and can exert both high acid-generating performance and high radical-generating performance, and has heat resistance; and a method for generating an acid and a radical.
The present invention relates to a compound represented by the general formula (A); an acid- and radical-generating agent comprising the compound; and a method for generating an acid and a radical:

wherein n pieces of R 1 each independently represent an alkyl group, which may have a specific functional group in the chain, or in which a hydrogen atom may be substituted by a halogen atom; an alkoxy group, in which a hydrogen atom may be substituted by a halogen atom; an aryl group or an aryloxy group, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; or an arylalkyl group or an arylalkyloxy group, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; n pieces of R 2 and R 3 each independently represent a hydrogen atom, an alkyl group or an alkoxycarbonyl group; R 4 to R 7 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an alkoxycarbonyl group, a dialkylamino group or a nitro group; Y represents an oxygen atom, a sulfur atom, or a carbonyl group; n pieces of Z each independently represent a sulfonyl group or an alkoxyphosphoryl group; n represents 1 or 2.

First claim

The invention claimed is:

1. A compound represented by the general formula (A):

wherein Y represents an oxygen atom, a sulfur atom, or a carbonyl group;

when Y represents a carbonyl group,
n pieces of R 1 each independently represent an alkyl group having 1 to 20 carbon atoms, which may have a functional group selected from the group consisting of a carbonyloxy group, a carbonylamino group, an ether group and a sulfide group in the chain, or in which a hydrogen atom may be substituted by a halogen atom; an aryloxy group having 6 to 10 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; an arylalkyl group having 7 to 15 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; or an arylalkyloxy group having 7 to 15 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group;
n pieces of R 2 and n pieces of R 3 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxycarbonyl group having 2 to 7 carbon atoms; R 4 to R 7 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, or a nitro group;
n pieces of Z each independently represent a sulfonyl group or an alkoxyphosphoryl group having 1 to 6 carbon atoms; and
n represents 1 or 2; and

when Y represents an oxygen atom or a sulfur atom,
n pieces of R 1 each independently represent an alkyl group having 1 to 20 carbon atoms, which may have a functional group selected from the group consisting of a carbonyloxy group, a carbonylamino group, an ether group and a sulfide group in the chain, or in which a hydrogen atom may be substituted by a halogen atom; an alkoxy group having 1 to 10 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom; an aryl group having 6 to 10 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; an aryloxy group having 6 to 10 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; an arylalkyl group having 7 to 15 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; or an arylalkyloxy group having 7 to 15 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group;
n pieces of R 2 and n pieces of R 3 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxycarbonyl group having 2 to 7 carbon atoms;
R 4 to R 7 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms, a dialkylamino group having 2 to 8 carbon atoms, or a nitro group;
n pieces of Z represent a sulfonyl group; and
n represents 1 or 2.

2. The compound according to claim 1 , wherein the compound represented by the general formula (A) is a compound represented by the general formula (A′-1):

wherein Y represents an oxygen atom, a sulfur atom, or a carbonyl group;

when Y represents a carbonyl group,
R 1a and R 1b each independently represent an alkyl group having 1 to 20 carbon atoms, which may have a functional group selected from the group consisting of a carbonyloxy group, a carbonylamino group, an ether group and a sulfide group in the chain, or in which a hydrogen atom may be substituted by a halogen atom; an aryloxy group having 6 to 10 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; an arylalkyl group having 7 to 15 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; or an arylalkyloxy group having 7 to 15 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group;
R 2a ,R 2b , R 3a and R 3b each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxycarbonyl group having 2 to 7 carbon atoms; and
Z a and Z b each independently represent a sulfonyl group or an alkoxyphosphoryl group having 1 to 6 carbon atoms; and
when Y represents an oxygen atom or a sulfur atom,
R 1a and R 1b each independently represent an alkyl group having 1 to 20 carbon atoms, which may have a functional group selected from the group consisting of a carbonyloxy group, a carbonylamino group, an ether group and a sulfide group in the chain, or in which a hydrogen atom may be substituted by a halogen atom; an alkoxy group having 1 to 10 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom; an aryl group having 6 to 10 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; an aryloxy group having 6 to 10 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; an arylalkyl group having 7 to 15 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; or an arylalkyloxy group having 7 to 15 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group;
R 2a , R 2b , R 3a and R 3b each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxycarbonyl group having 2 to 7 carbon atoms; and
Z a and Z b represent a sulfonyl group;
R 4 to R 7 are the same as described above.

3. The compound according to claim 1 , wherein the compound represented by the general formula (A) is a compound represented by the general formula (A′-2):

wherein Y represents an oxygen atom, a sulfur atom, or a carbonyl group;

when Y represents a carbonyl group,
R 1c represents an alkyl group having 1 to 20 carbon atoms, which may have a functional group selected from the group consisting of a carbonyloxy group, a carbonylamino group, an ether group and a sulfide group in the chain, or in which a hydrogen atom may be substituted by a halogen atom; an aryloxy group having 6 to 10 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; an arylalkyl group having 7 to 15 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group; or an arylalkyloxy group having 7 to 15 carbon atoms, in which a hydrogen atom may be substituted by a halogen atom, an alkyl group or a haloalkyl group;
R 2c and R 3c each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxycarbonyl group having 2 to 7 carbon atoms; and

Z c represents a sulfonyl group or an alkoxyphosphoryl group having 1 to 6 carbon atoms; and
when Y represents an oxygen atom or a sulfur atom,
R 1c represents an alkyl group having 1 to 20 carbon atoms, which may have a functional group selected from the group consisting of a carbonyloxy group, a carbonylamino group, an ether group

Assignees

• Fujifilm Wako Pure Chemical Corp

Inventors

• Sakai Nobuhiko
• YANABA Kosuke

Classifications

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• C07C317/24

  having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton · CPC title

• C07D335/16 Primary

  Oxygen atoms, e.g. thioxanthones · CPC title

• C07C317/44

  having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton · CPC title

• C07C2603/24

  Anthracenes; Hydrogenated anthracenes · CPC title