Method for producing thick film photoresist pattern

Patent metadata

Field	Value
Publication number	US-9244354-B2
Application number	US-201213708081-A
Country	US
Kind code	B2
Filing date	Dec 7, 2012
Priority date	Dec 16, 2011
Publication date	Jan 26, 2016
Grant date	Jan 26, 2016

Abstract

A method for producing a thick film photoresist pattern including laminating a thick photoresist layer including a chemically amplified positive-type photoresist composition for thick film on a support; irradiating the thick photoresist layer; and developing the thick photoresist layer to obtain a thick film resist pattern; in which the composition includes an acid generator, a resin whose alkali solubility increases by the action of an acid, and an organic solvent having a boiling point of at least 150° C. and a contact angle on a silicon substrate of no greater than 18°, in an amount of at least 40% by mass with respect to total mass of the organic solvent.

First claim

What is claimed is:

1. A method for producing a thick film photoresist pattern, comprising:
laminating a thick photoresist layer comprising a chemically amplified positive-type photoresist composition for thick film on a support;
irradiating the thick photoresist layer with an active ray or radiation; and
developing the thick photoresist layer following the irradiating to obtain a thick film resist pattern;
wherein:
the chemically amplified positive-type photoresist composition for thick film comprises an acid generator (A) capable of producing an acid upon irradiation with the active ray or radiation, a resin (B) whose alkali solubility increases by the action of an acid, and an organic solvent (S);
wherein the acid generator (A) is a compound represented by the following general formula (a1), a halogen-containing triazine compound, a compound represented by the following general formula (a4) or a compound composed of a cation moiety represented by the following general formula (a5) and an anion moiety represented by the following general formula (a9), (a13) or (a14);

in the above general formula (a1), X 1a represents a sulfur atom or an iodine atom having a valency of g; g is 1 or 2; h represents the number of repeating units represented by the structure in the parentheses; R 1a represents an organic group attached to X 1a and represents an aryl group having 6 to 30 carbon atoms, a heterocyclic group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms or an n 1 group having 2 to 30 carbon atoms; R 1a may be substituted with at least one selected from the group consisting of an alkyl group, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, a heterocyclic group, an aryloxy group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, arylsulfonyl, an alkyleneoxy group, an amino group, a cyano group, a nitro group and a halogen atom; the number of R 1a is g+h(g−1)+1, each R 1a may be identical or different from each other; also, at least two R 1a may bond to each other directly or via —O—, —S—, —SO—, —SO 2 —, —NH—, —NR 2a —, —CO—, —COO—, —CONH—, an alkylene group having 1 to 3 carbon atoms, or phenylene groups, to form a ring structure containing X 1a ; and R 2a represents an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 10 carbon atoms;
in the above general formula (a1), X 2a represents a structure represented by the following general formula (a2);

in the above general formula (a2), X 4a represents an alkylene group having 1 to 8 carbon atoms, an arylene group having 6 to 20 carbon atoms or a divalent group derived from a heterocyclic compound having 8 to 20 carbon atoms; X 4a may be substituted with at least one selected from the group consisting of an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, a hydroxy group, a cyano group, a nitro group and a halogen atom; X 5a represents —O—, —S—, —SO—, —SO 2 —, —NH—, —NR 2a —, —CO—, —COO—, —CONH—, an alkylene group having 1 to 3 carbon atoms or a phenylene group; h represents the number of repeating units of the structure in the parentheses; h+1 X 4a 's and h X 5a 's may be each identical or different from each other, and R 2a represents an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 10 carbon atoms;
in the above general formula (a1), X 3a− represents a counterion of the onium, and is a fluorinated alkyl fluorophosphate anion represented by the following general formula (a17) or a borate anion represented by the following general formula (a18);
[(R 3a ) j PF 6-i ] −   (a17)

in the above general formula (a17), R 3a represents an alkyl group of which no less than 80% of the hydrogen atoms are substituted with a fluorine atom; j represents an integer of 1 to 5; and j R 3a 's ma be identical or different from each other;

in the above general formula (a18), R 4a to R 7a each independently represent a fluorine atom or a phenyl group, and a part or all hydrogen atoms of the phenyl group may be substituted with at least one selected from the group consisting of a fluorine atom and a trifluoromethyl group;
the halogen-containing triazine compound is selected from the group consisting of 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(2-furyl)ethenyl]-s-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methyl-2-furyl)ethenyl]-s-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-ethyl-2-furyl)ethenyl]-s-triazine 2,4-bis(trichloromethyl)-6-[2-(5-propyl-2-furyl)ethenyl]-s-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,5-dimethoxyphenyl)ethenyl]-s-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,5-diethoxyphenyl)ethenyl]-s-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,5-dipropoxyphenyl)ethenyl]-s-triazine, 2,4-bis(trichloromethyl)-6-[2-(3-methoxy-5-ethoxyphenyl)ethenyl]-s-triazine, 2,4-bis(trichloromethyl)-6-[2-(3-methoxy-5-propoxyphenyl)ethenyl]-s-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-methylenedioxyphenyl)ethenyl]-s-triazine, 2,4-bis(trichloromethyl)-6-(3,4-methylenedioxyphenyl)-s-triazine, 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxy)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(2-bromo-4-methoxy)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(2-bromo-4-methoxy)styrylphenyl-s-triazine 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxy)styrylphenyl-s-triazine, 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-(4-methoxynaphthyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-(2-furyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-(5-methyl-2-furyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-(3,5-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine 2-(3,4-methylenedioxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, tris(1,3-dibromopropyl)-1,3,5-triazine, tris(2,3-dibromopropyl)-1,3,5-triazine, and compounds represented by the following general formula (a3)

in the above general formula (a3), R 9a , R 10a and R 11a each independently represent a halogenated alkyl group;

in the above general formula (a4), R 12a represents a monovalent, bivalent or trivalent organic group; R 13a represents a substituted or unsubstituted saturated hydrocarbon group, an unsaturated hydrocarbon group, or an aromatic compound group; and n represents the number of repeating units of the structure in the parentheses;

in the above general formula (a5), at least one of R 14a , R 15a and R 16a represents a group represented by the following general formula (a6); the remaining represents a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group which may have a substituent, a hydroxyl group, or a linear or branched alkoxy group having 1 to 6 carbon atoms; alternatively, one of R 14a , R 15a and R 16a is a group represented by the follow

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Washio Yasushi
• Ando Tomoyuki
• Shimura Eiichi
• Tachi Toshiaki

Classifications

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/0048

  characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents · CPC title

• G03F7/20 Primary

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title

• G03F7/0392 Primary

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title