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US 9,897,913 B2Granted
Radiation-sensitive composition
AssigneeMitsubishi Gas Chemical Company, Inc.
InventorsMasatoshi Echigo, Dai Oguro
Life of this patent
Estimating the term…
Abstract
A radiation-sensitive composition containing a resist compound having a high sensitivity, a high resolution, a high etching resistance, and a low outgas which forms a resist pattern with a good shape is described.
Claims5
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 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 5 to 6, 10, and 12 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 2 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 5.
5 more elements
A radiation-sensitive composition comprising a cyclic compound (B) represented by the following formula (19-1) and a low molecular weight solubilizer (D):
- wherein 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, and a cyclic ether group having 2 to 20 carbon atoms;
- 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, 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;
- and
- p is an integer of 1 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.
2 more elements
A radiation-sensitive composition comprising 1 to 80% by weight of a solid component and 20 to 99% by weight of the solvent,
- wherein the radiation-sensitive composition contains the cyclic compound (B) having a structure obtained by introducing an acid-dissociating functional group into at least one phenolic hydroxyl group of a cyclic compound (A) having a molecular weight of 700 to 5000 which 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,
- wherein the cyclic compound (B) is contained in an amount of 50 to 99.999% by weight a total weight of the solid component, and
- wherein the compound (A) is selected from the group consisting of the cyclic compounds of formula (2-1), and formula (2-2):
- wherein in the formulae (2-1) and (2-2) the group R7A is independently a hydrogen atom, a linear alkyl group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a hydroxyl group, an alkoxyl group, or an ester group.
1 more element
A radiation-sensitive composition comprising 1 to 80% by weight of a solid component and 20 to 99% by weight of the solvent,
- wherein the radiation-sensitive composition contains the cyclic compound (B) having a structure obtained by introducing an acid-dissociating functional group into at least one phenolic hydroxyl group of a cyclic compound (A) having a molecular weight of 700 to 5000 which 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,
- wherein the cyclic compound (B) is contained in an amount of 50 to 99.999% by weight a total weight of the solid component, and
- wherein the compound (A) is selected from the group consisting of the cyclic compounds of formula (33-1), formula (33-2), formula (33-0-1) and formula (33-0-2):
- wherein in the formula (33-1), (33-2), (33-0-1) and (33-0-2), R3A is a substituted methyl group selected from the group consisting of n-propoxymethyl group, isopropoxymethyl group, n-butoxymethyl group, t-butoxymethyl group, 2-methylpropoxymethyl group, ethylthiomethyl group, methoxyethoxymethyl group, phenyloxymethyl group, 1-cyclopentyloxymethyl group, 1-cyclohexyloxymethyl group, benzylthiomethyl group, phenacyl, 4-bromophenacyl, 4-methoxyphenacyl, piperonyl group, and the groups represented by the following formula (7):
- R2 is an alkyl group having 1 to 4 carbon atoms,
- X2 is a 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 or 2, and
- m4 is 1.
8 more elements
A radiation-sensitive composition comprising 1 to 80% by weight of a solid component and 20 to 99% by weight of the solvent,
- wherein the radiation-sensitive composition contains the cyclic compound (B) having a structure obtained by introducing an acid-dissociating functional group into at least one phenolic hydroxyl group of a cyclic compound (A) having a molecular weight of 700 to 5000 which 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,
- wherein the cyclic compound (B) is contained in an amount of 50 to 99.999% by weight a total weight of the solid component, and
- wherein the compound (A) is selected from the group consisting of the cyclic compounds of formula (33-1), formula (33-2), formula (33-0-1) and formula (33-0-2);
- wherein in the formula (33-1), (33-2), (33-0-1) and (33-0-2), R3A is a 1-substituted alkoxyalkyl group selected from the group consisting of 1-cyclopentylmethoxymethyl group, 1-cyclopentylethoxymethyl group, 1-cyclohexylmethoxymethyl group, 1-cyclohexylethoxymethyl group, 1-cyclooctylmethoxymethyl group, and 1-adamantylmethoxymethyl group,
- X2 is a 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 or 2, and
- m4 is 1.
7 more elements
Dependencies are inferred from the claim text.