US 2005/0233253 A1 · Heterocycle-bearing onium salts

Abstract

The present invention relates to a heterocycle-containing onium salt useful as, for example, a cationic photopolymerization initiator and an acid generator for a chemically amplified resist, and provides “a heterocycle-containing onium salt shown by the general formula [1]: [wherein R is a group shown by the general formula [2]: (wherein R3 and R4 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or a lower alkyl group as a substituent; X2 is an oxygen atom or a sulfur atom; i is an integer of 0 to 4; and j is an integer of 0 to 3), or a group shown by the general formula [3]: (wherein R5 and R6 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or a lower alkyl group as a substituent; X3 and X4 are each independently an oxygen atom or a sulfur atom; p is an integer of 0 to 2; and q is an integer of 0 to 3); R1 and R2 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or a lower alkyl group as a substituent; m and n are each independently an integer of 0 to 5; and A is a halogen atom or an anion derived from an inorganic strong acid, an organic acid or a compound shown by the general formula [4]: HM1(R7)4 [4] (wherein M1 is a boron atom or a gallium atom; and R7 is an aryl group which may have a substituent selected from a lower haloalkyl group, a halogen atom, a nitro group and a cyano group)]” or “a heterocycle-containing onium salt shown by the general formula [35]: [wherein R26 and R27 are each independently an aryl group which may have a halogen atom or a lower alkyl group as a substituent, a group shown by the above-mentioned general formula [2], or a group shown by the above-mentioned general formula [3]; and A3 is a halogen atom or an anion derived from an inorganic strong acid, an organic acid or a compound shown by the general formula [4]; and provided that at least one of R26 and R27 is a group shown by the above-mentioned general formula [2] or [3], and when only one of R26 and R27 is a group shown by the above-mentioned general formula [2] or [3], A3 is an anion derived from an inorganic strong acid shown by the general formula [36]; HM3F6 [36] (wherein M3 is a phosphorus atom, an arsenic atom or an antimony atom), an organic acid or a compound shown by the general formula [4]]”.

Claims37

Dependent claims

A heterocycle-containing onium salt shown by the general formula [1] or [35]:

[wherein R is a group shown by the general formula [2]:
(wherein R3 and R4 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent;
X2 is an oxygen atom or a sulfur atom;
i is an integer of 0 to 4;
and j is an integer of 0 to 3), or a group shown by the general formula [3]:
(wherein R5 and R6 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent;
X3 and X4 are each independently an oxygen atom or a sulfur atom;
p is an integer of 0 to 2;
and q is an integer of 0 to 3);
R1 and R2 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent;
m and n are each independently an integer of 0 to 5;
and A is a halogen atom or an anion derived from an inorganic strong acid, an organic acid or a compound shown by the general formula [4]:
HM1(R7)4 [4]
(wherein M1 is a boron atom or a gallium atom;
and R7 is an aryl group which may have a substituent selected from a haloalkyl group having 1 to 6 carbon atoms, a halogen atom, a nitro group and a cyano group)],
R26—I⊕—R27A3 [35]
[wherein R26 and R27 are each independently an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent, a group shown by the above-mentioned general formula [2], or a group shown by the above-mentioned general formula [3];
A3 is a halogen atom or an anion derived from an inorganic strong acid, an organic acid or a compound shown by the general formula [4];
and provided that at least one of R26 and R27 is a group shown by the above-mentioned general formula [2] or [3], and when only one of R26 and R27 is a group shown by the above-mentioned general formula [2] or [3], A3 is an anion derived from an inorganic strong acid shown by the general formula [36];
HM3F6 [36]
(wherein M3 is a phosphorus atom, an arsenic atom or an antimony atom), an organic acid or a compound shown by the general formula [4]].

18 more elements

A cationic photopolymerization initiator comprising a heterocycle-containing onium salt shown by the general formula [8]:

[wherein R is a group shown by the general formula [2]:
(wherein R3 and R4 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent;
X2 is an oxygen atom or a sulfur atom;
i is an integer of 0 to 4;
and j is an integer of 0 to 3), or a group shown by the general formula [3]:
(wherein R5 and R6 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent;
X3 and X4 are each independently an oxygen atom or a sulfur atom;
p is an integer of 0 to 2;
and q is an integer of 0 to 3);
R1 and R2 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent;
m and n are each independently an integer of 0 to 5;
and A1 is an anion derived from an inorganic strong acid, a sulfonic acid or a compound shown by the general formula [4]:
HM1(R7)4 [4]
(wherein M1 is a boron atom or a gallium atom;
R7 is an aryl group which may have a substituent selected from a haloalkyl group having 1 to 6 carbon atoms, a halogen atom, a nitro group and a cyano group)].

12 more elements

A cationic photopolymerization initiator comprising a heterocycle-containing iodonium salt shown by the general formula [37]:

R26—I⊕—R27A4 [37]
[wherein R26 and R27 are each independently an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent, a group shown by the general formula [2]:
(wherein R3 and R4 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent;
X2 is an oxygen atom or a sulfur atom;
i is an integer of 0 to 4;
and j is an integer of 0 to 3), or a group shown by the general formula [3]:
(wherein R5 and R6 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent;
X3 and X4 are each independently an oxygen atom or a sulfur atom;
p is an integer of 0 to 2;
and q is an integer of 0 to 3);
and A4 is an anion derived from an inorganic strong acid, a sulfonic acid or a compound shown by the general formula [4]:
HM1(R7)4 [4]
(wherein M1 is a boron atom or a gallium atom;
R7 is an aryl group which may have a substituent selected from a haloalkyl group having 1 to 6 carbon atoms, a halogen atom, a nitro group and a cyano group);
and provided that at least one of R26 and R27 is a group shown by the above-mentioned general formula [2] or [3], and when only one of R26 and R27 is a group shown by the above-mentioned general formula [2] or [3], an inorganic strong acid is one shown by the general formula [36]:
HM3F6 [36]
(wherein M3 is a phosphorus atom, an arsenic atom or an antimony atom)].

14 more elements

An acid generator for a resist, comprising an iodonium salt shown by the general formula [38]:

R26—I⊕—R27A5 [38]
[wherein R26 and R27 are each independently an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent, a group shown by the general formula [2]:
(wherein R3 and R4 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent;
X2 is an oxygen atom or a sulfur atom;
i is an integer of 0 to 4;
and j is an integer of 0 to 3), or a group shown by the general formula [3]:
(wherein R5 and R6 are each independently a halogen atom, an alkyl group which may have a halogen atom or an aryl group as a substituent, or an aryl group which may have a halogen atom or an alkyl group having 1 to 6 carbon atoms as a substituent;
X3 and X4 are each independently an oxygen atom or a sulfur atom;
p is an integer of 0 to 2;
and q is an integer of 0 to 3);
and A5 is an anion derived from an inorganic strong acid, an organic acid or a compound shown by the general formula [4]:
HM1(R7)4 [4]
(wherein M1 is a boron atom or a gallium atom;
and R is an aryl group which may have a substituent selected from a haloalkyl group having 1 to 6 carbon atoms, a halogen atom, a nitro group and a cyano group);
and provided that at least one of R26 and R27 is a group shown by the above-mentioned general formula [2] or [3], and when only one of R26 and R27 is a group shown by the above-mentioned general formula [2] or [3], an inorganic strong acid is one shown by the general formula [36]:
HM3F6 [36]
(wherein M3 is a phosphorus atom, an arsenic atom or an antimony atom)].

14 more elements

Dependencies are inferred from the claim text.

Heterocycle-bearing onium salts

Life of this patent

Heterocycle-bearing onium salts

Life of this patent

Abstract

Claims37