Acid- and radical-generating agent and method for generating acid and radical
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.
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 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 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;
R 4 to R 7 are the same as described above.
4. 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 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; and
R 2a , R 2b , R 3b 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 7carbon atoms.
5. 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 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; and
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.
6. 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 R 1a and R 1b each independently represent an alkyl group having 1 to 15 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 fluorine 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.
7. 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 R 1c represents an alkyl group having 1 to 15 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 fluorine 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.
8. The compound according to claim 1 , wherein the compound represented by the general formula (A) is the one represented by the formula (1), the formula (2), the formula (3), the formula (4), the formula (5), or the formula (8):
9. An acid- and radical-generating agent comprising the compound according to claim 1 .
10. The acid- and radical-generating agent according to claim 9 , wherein the acid- and radical-generating agent is the one generating an acid and a radical by irradiation of an active energy ray.
11. A method for generating an acid and a radical, which comprises irradiating an active energy ray onto the compound according to claim 1 .
12. The method for generating an acid and a radical according to claim 11 , wherein main wavelength of the active energy ray is 405 nm.