Radiation-sensitive composition

A radiation-sensitive composition comprising a cyclic compound represented by the following formula (1), a solvent and an acid crosslinking agent (G):

• wherein L is independently a divalent organic group selected from the group consisting of a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, an arylene group having 6 to 24 carbon atoms, —O—, —OC(═O)—, —OC(═O)O—, —N(R5)—C(═O)—, —N (R5)—C(═O)O—, —S—, —SO—, —SO2—, and any combination of the preceding groups;
• R1 is independently hydrogen atom, a functional group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, cyano group, nitro group, hydroxyl group, heterocyclic group, halogen atom, carboxyl group, an alkylsilyl group having 1 to 20 carbon atoms, and a group derived from the preceding groups, or an acid-dissociating functional group selected from the group consisting of a substituted methyl group having 2 to 20 carbon atoms, a 1-substituted ethyl group having 3 to 20 carbon atoms, a 1-substituted n-propyl group having 4 to 20 carbon atoms, a 1-branched alkyl group having 3 to 20 carbon atoms, a silyl group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, a 1-substituted alkoxyalkyl group having 2 to 20 carbon atoms, a cyclic ether group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms and an alkoxycarbonylalkyl group;
• R′ is independently an alkyl group having 2 to 20 carbon atoms, an aryl group having 6 to 24 carbon atoms represented by the following formula:
• or a group derived from the preceding groups;
• R4 is a functional group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms exclusive of t-butyl group, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, cyano group, nitro group, heterocyclic group, halogen atom, carboxyl group, an alkylsilyl group having 1 to 20 carbon atoms, and a group derived from the preceding groups, or an acid-dissociating functional group selected from the group consisting of a substituted methyl group having 2 to 20 carbon atoms, a 1-substituted ethyl group having 3 to 20 carbon atoms, a 1-substituted n-propyl group having 4 to 20 carbon atoms, a 1-branched alkyl group having 3 to 20 carbon atoms, a silyl group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, a 1-substituted alkoxyalkyl group having 2 to 20 carbon atoms, a cyclic ether group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms and an alkoxycarbonylalkyl group;
• R5 is hydrogen atom or an alkyl group having 1 to 10 carbon atoms;
• m is an integer of 1 to 4;
• and p is an integer of 0 to 5.

A radiation-sensitive composition comprising a cyclic compound (B) represented by the following formula (19-1) and a low-molecular weight solubilizer (D):

• cyclic compound (B) is represented by the following formula (19-1);
• wherein RI is independently hydrogen atom, a functional group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, cyano group, nitro group, hydroxyl group, heterocyclic group, halogen atom, carboxyl group, an alkylsilyl group having 1 to 20 carbon atoms, and a group derived from the preceding groups, or an acid-dissociating functional group selected from the group consisting of a substituted methyl group having 2 to 20 carbon atoms, a 1-substituted ethyl group having 3 to 20 carbon atoms, a 1-substituted n-propyl group having 4 to 20 carbon atoms, a • 1-branched alkyl group having 3 to 20 carbon atoms, a silyl group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, a 1-substituted alkoxyalkyl group having 2 to 20 carbon atoms, a cyclic ether group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms and an alkoxycarbonylalkyl group;
• R4 is a functional group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms exclusive of t-butyl group, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, cyano group, nitro group, heterocyclic group, halogen atom, carboxyl group, an alkylsilyl group having 1 to 20 carbon atoms, and a group derived from the preceding groups, or an acid-dissociating functional group selected from the group consisting of a substituted methyl group having 2 to 20 carbon atoms, a 1-substituted ethyl group having 3 to 20 carbon atoms, a 1-substituted n-propyl group having 4 to 20 carbon atoms, a 1-branched alkyl group having 3 to 20 carbon atoms, a silyl group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, a 1-substituted alkoxyalkyl group having 2 to 20 carbon atoms, a cyclic ether group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms and an alkoxycarbonylalkyl group;
• R5 is hydrogen atom or an alkyl group having 1 to 10 carbon atoms;
• m is an integer of 1 to 4;
• and p is an integer of 0 to 5,
• wherein the cyclic compound (B) is contained in an amount of 50 to 99.999% by weight a total weight of the solid components.

A method of producing a cyclic compound (B0), comprising a first stage reaction which an aldehyde compound in which an aldehyde compound (A1b) having from 2 to 59 carbon atoms, a reactive functional group and from 1 to 4 formyl groups is allowed to react with a reagent for introducing an acid-dissociating functional group, thereby synthesizing an aldehyde compound (A1c) having the acid-dissociating functional group introduced, and a second stage reaction in which the aldehyde compound (A1c) and a phenol compound (A2) are subjected to a condensation reaction, wherein the aldehyde compound (A1c) is represented by the following formula (47):

• wherein L is a divalent organic group selected from the group consisting of a single bond, an alkylene group having 1 to 20 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, —O—, —OC(═O)—, —OC(═O)O—, —N(R5)—C(═O)—, —N(R5)—C(═O)O—, —S—, —SO—, —SO2—, and any combination of the preceding groups;
• R1 is hydrogen atom or an acid-dissociating functional group selected from the group consisting of a substituted methyl group having 2 to 20 carbon atoms, a 1-substituted ethyl group having 3 to 20 carbon atoms, a 1-substituted n-propyl group having 4 to 20 carbon atoms, a 1-branched alkyl group having 3 to 20 carbon atoms, a silyl group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, a 1-substituted alkoxyalkyl group having 2 to 20 carbon atoms, a cyclic ether group having 2 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, and an alkoxycarbonylalkyl group;
• R2 is hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, cyano group, nitro group, hydroxyl group, a heterocyclic group, a halogen atom, carboxyl group, an alkylsilyl group having 1 to 20 carbon atoms, or a functional group selected from derivatives of the preceding groups;
• R5 is hydrogen atom or an alkyl group having 1 to 10 carbon atoms;
• m1 is an integer of 1 to 5 and m2 is an integer of 0 to 4 satisfying m1+m2=5.