Radiation-sensitive composition

A method of producing a cyclic compound chosen from

• wherein R3A is 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 having 2 to 20 carbon atoms;
• and X2 is hydrogen atom or a halogen atom;
• L1 is a single bond or a divalent organic group selected from a linear or branched alkylene group having 1 to 4 carbon atoms;
• l1 is 0 or 1;
• m is an integer of 1 to 4, m3 is an integer of 1 to 2;
• and m4 is 1, comprising a first stage reaction in which an aldehyde compound (A1d) having 2 to 59 carbon atoms, 1 to 4 formyl groups, and 1 to 2 carboxyl groups or ester groups and a phenol compound (A2) are subjected to a condensation reaction, thereby synthesizing a cyclic compound (A0) having 1 to 8 carboxyl groups and a molecular weight of 800 to 5000, and a second stage reaction in which the cyclic compound (A0) is allowed to react with a compound (A3) having a halomethyl ether group.

A composition comprising a resin having repeating units derived from a water-eliminating condensation of a cyclic compound represented by the following formula (1):

• wherein L is independently a divalent organic group selected from 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 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 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 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 1 to 3 with an aldehyde compound (A1a) in the presence of an acid catalyst, wherein the cyclic compound according to formula (1) has a molecular weight of 700 to 5000 and is synthesized by a condensation reaction of an aldehyde compound (A1) having 2 to 59 carbon atoms and 1 to 4 formyl groups with a phenol compound (A2) having 6 to 15 carbon atoms and 1 to 3 phenolic hydroxyl groups.