CN112485963A - KrF thick film photoresist additive and photoresist composition containing same - Google Patents

KrF thick film photoresist additive and photoresist composition containing same Download PDF

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CN112485963A
CN112485963A CN202011360612.3A CN202011360612A CN112485963A CN 112485963 A CN112485963 A CN 112485963A CN 202011360612 A CN202011360612 A CN 202011360612A CN 112485963 A CN112485963 A CN 112485963A
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phenyl
alkyl
substituted
photoresist composition
photoacid generator
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王溯
方书农
耿志月
崔中越
唐晨
薛新斌
王世建
王志勇
张君
霍静静
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Shanghai Xinyang Semiconductor Material Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
    • H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
    • H01L21/0274—Photolithographic processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)

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Abstract

The invention discloses a KrF thick film photoresist additive and a photoresist composition containing the same. Specifically, the invention provides a photoresist composition, which is prepared from the following raw materials: plasma light absorbers, photoacid generators, photosensitive polymers, and organic solvents; wherein the plasma light absorber is an acylphosphine oxide compound shown in formula (I). The acyl phosphine oxide light absorber and the conventional photoacid generator in the photoresist composition provided by the invention are cooperatively matched to generate better light transmittance, so that when the photoresist composition provided by the invention is used together with deep ultraviolet light, a photoresist pattern which has large thickness and can realize high-quality etching of a lower layer can be formed.

Description

KrF thick film photoresist additive and photoresist composition containing same
Technical Field
The present invention relates to photoresist compositions for KrF light source (248nm) Deep Ultraviolet (DUV) light.
Background
Currently, in the field of semiconductor manufacturing, during the chip manufacturing process of LCD (liquid crystal display)/BUMP/MEMS micro-electro-mechanical system/3D-NAND memory, KrF light source thick film photoresist is used, which is different from the conventional KrF thin layer photoresist and the ArF light source photoresist, but has unique performance.
However, when the photoresist pattern is thick, the light transmittance of the photoresist may become a problem, and thus work to increase the light transmittance is required. However, the work of improving light transmittance involves a plurality of optical problems, and thus a plurality of technical problems should be solved at the same time.
In patent CN109581810A, a phenol compound having an electron donating substituent at the ortho-position of a hydroxyl group and an electron withdrawing substituent at the para-position or meta-position thereof is used as a selective light absorber to selectively increase the light transmittance. However, the variety of photoacid generators available for use is limited, and the effect is not ideal for the widely used conventional photoacid generators such as Triphenylsulfonium (TPS). This greatly limits the range of applications.
In addition, conventional photoacid generators such as Triphenylsulfonium (TPS), which are widely used, have many advantageous properties in their own right as compared to other types of photoacid generators. Therefore, it is an urgent technical problem in the art to find a plasma light absorber capable of cooperating with triphenylsulfonium to generate excellent light transmittance.
Disclosure of Invention
In order to solve the above-mentioned technical problems, a first aspect of the present invention provides a photoresist composition, which is characterized by being prepared from the following raw materials: plasma light absorbers, photoacid generators, photosensitive polymers, and organic solvents; wherein the plasma light absorber is an acylphosphine oxide compound shown as a formula (I),
Figure BDA0002803808720000011
wherein m is 1 or 2;
x is oxygen or sulfur;
R1and R3Are each independently C1-4Alkyl, phenyl, -C (O) -phenyl, C (O) -phenyl1-4Phenyl substituted by alkyl, or by C1-4Alkyl-substituted-c (o) -phenyl;
R2is C1-4Alkyl, phenyl, or by C1-4Alkyl-substituted phenyl;
and R is1、R2And R3Not all are C1-4An alkyl group.
In the acyl phosphine oxide compound shown in the formula (I), m and R1、R2And R3May be as defined in one of (a) - (e):
(a) m is 1, R1And R3Is phenyl, R2Is a quilt C1-4Alkyl-substituted phenyl;
(b) m is 1, R1And R3One of which is phenyl and the other is C1-4alkyl-substituted-C (O) -phenyl, R2Is C1-4An alkyl group;
(c) m is 2, R1Is phenyl, R2Is a quilt C1-4Alkyl-substituted phenyl, R3Is absent;
(d) m is 2, R1Is a quilt C1-4alkyl-substituted-C (O) -phenyl, R2Is a quilt C1-4Alkyl-substituted phenyl, R3Is absent; or
(e) m is 2, R1Is phenyl; r2Is C1-4Alkyl radical, R3Is absent.
In the acylphosphine oxide compound represented by the formula (I), X may be oxygen.
In the acylphosphine oxide compound shown in the formula (I), R1、R2And R3C as described in (1)1-4The alkyl group may be a tert-butyl group.
In the acylphosphine oxide compound shown in the formula (I), R1And R3The quilt of (1)1-4The alkyl-substituted phenyl group may be
Figure BDA0002803808720000021
For example,
Figure BDA0002803808720000022
in the acylphosphine oxide compound shown in the formula (I), R1And R3The quilt of (1)1-4The alkyl-substituted-C (O) -phenyl group may be
Figure BDA0002803808720000023
In one embodiment of the photoresist composition, the plasma light absorber can be:
Figure BDA0002803808720000024
Figure BDA0002803808720000031
for example,
Figure BDA0002803808720000032
as another example of the present invention,
Figure BDA0002803808720000033
in a certain embodiment of the photoresist composition, the maximum absorbance of light in a first wavelength range by the plasma light absorber can be less than 0.25 times, such as 0.01 times to 0.25 times, such as 0.05 times to 0.2 times, and such as 0.1 times to 0.15 times, the maximum absorbance of light in a second wavelength range by the plasma light absorber, wherein the first wavelength range is 240nm to 255nm, and the second wavelength range is 270nm to 330 nm.
In certain embodiments of the photoresist composition, the plasma light absorber can have a high transmittance for light in a wavelength band, e.g., 248nm, which can be beneficial for exposure processes using Deep Ultraviolet (DUV) light (ultraviolet light having a wavelength from about 200nm to about 280nm, e.g., 248nm), and more particularly, for exposure processes using krypton fluoride (KrF) lasers. The plasma light absorber may absorb light emitted by plasma generated during the dry etching process.
The maximum transmittance of the plasmonic light absorber for light of the first wavelength range may be more than 1.5 times, such as 1.5 times to 2 times, further such as 1.5 times to 1.8 times, further such as 1.6 times to 1.7 times, the maximum transmittance of the plasmonic light absorber for light of the second wavelength range.
Since the plasma light absorber transmits light of the first wavelength range well, the plasma light absorber does not inhibit a photochemical reaction of the photopolymer during exposure using the KrF excimer laser even when included in the photoresist composition. Since the plasma light absorber well absorbs the light of the second wavelength range, it is possible to effectively absorb the light emitted by the plasma (and mainly having a peak in the second wavelength range) during the dry etching using the photoresist pattern formed from the photoresist composition.
The photosensitive polymer that has not reacted is present in the photoresist pattern. When light emitted from the plasma is not blocked during etching, the photopolymer may also undergo a photochemical reaction during etching, thereby possibly degrading the quality of etching. Thus, by blocking light emitted from the plasma, photochemical reactions of the photopolymer during etching can be suppressed, and improved etching can be achieved.
In one embodiment of the photoresist composition, the plasma light absorber can be present in an amount conventional to photoresists used in the art, for example, in a mass fraction of 0.5 wt% to 2 wt% (e.g., 0.7 wt% to 1.3 wt%, again e.g., 1 wt%) of the plasma light absorber as a percentage of the mass of the plasma light absorber to the total mass of the starting materials. When the content of the plasma light absorber is too low, for example, less than 0.5 wt%, the effect achieved by adding the plasma light absorber may be insufficient for some semiconductor processes; and when the content of the plasma light absorber is too high, for example, more than 2 wt%, an improper photoresist pattern may be formed for a different semiconductor process.
Photoacid generators
In one embodiment of the photoresist composition, the photoacid generator can be a photoacid generator conventionally used in photoresists of the art, e.g., the cation of the photoacid generator can be a phenylsulfonium cation of formula (II) and/or a phenyliodonium cation of formula (III),
Figure BDA0002803808720000041
wherein R is3And R4Independently is phenyl, carboxy, -C1-60alkylene-COOH, RaSubstituted or unsubstituted C1-60Alkyl radical, RaSubstituted or unsubstituted C1-60Alkoxy radical, RaSubstituted or unsubstituted C2-60Alkenyl radical, RaSubstituted or unsubstituted C2-60Alkynyl, or RaSubstituted or unsubstituted C3-60A cycloalkyl group; raIndependently is C1-6Alkyl radical, C1-6Alkoxy radical, C6-12Aromatic ring, halogen atom, OH, NH2An aldehyde group or a carboxyl group.
In one embodiment of the photoresist composition, the cation of the photoacid generator can be
Figure BDA0002803808720000042
Figure BDA0002803808720000043
For example,
Figure BDA0002803808720000044
in one embodiment of the photoresist composition, the anion of the photoacid generator can be a non-nucleophilic anion conventional in photoacid generators in the art; for example, the anion of the photoacid generator may be a halogen ion, (R)7(SO2))(R8(SO2))N-、(R7(SO2))(R8(SO2))(R9(SO2))C-Or R10(SO3)-(ii) a Wherein R is7、R8、R9Each independently of the other being completely fluorinated C2-4Alkyl, completely fluorinated phenyl, -phenyl- (completely fluorinated or unsubstituted C2-46Alkyl), - (completely fluorinated C)2-4Alkylene) -O-completely fluorinated C2-C4Alkyl, - (completely fluorinated C)2-4Alkylene) -a completely fluorinated 6-membered heterocycle containing 1 oxygen atom, or- (C)1-3Alkylene) - (a 7-to 10-membered bridged ring containing a C ═ O group); or, R7、R8Is connected to contain- (SO)2)N-(SO2) -a fully fluorinated 6-8 membered heterocyclic ring; r10Is completely fluorinated or unsubstituted C6-10Aryl or completely fluorinated or unsubstituted C1-10An alkyl group.
In one embodiment of the photoresist composition, the anion of the photoacid generator can be a trifluoromethanesulfonate ion.
In one embodiment of the photoresist composition, the photoacid generator can be
Figure BDA0002803808720000051
Figure BDA0002803808720000052
For example,
Figure BDA0002803808720000053
in one embodiment of the photoresist composition, the photoacid generator can be present in an amount conventional to those used in photoresists of the art, e.g., in a mass fraction of 1 wt% to 10 wt% (e.g., 3 wt% to 8 wt%, again e.g., 5 wt%) of the photoacid generator as a percentage of the mass of the photoacid generator relative to the total mass of starting materials. When the content of the photoacid generator is too low, for example, less than 1 wt%, chemical amplification may be insufficient; when the content of the photoacid generator is too high, for example, more than 10 wt%, a product such as hydrogen may be excessively generated to degrade the quality of the material layer.
In one embodiment of the photoresist composition, the plasma light absorber can be
Figure BDA0002803808720000054
The photoacid generator can be
Figure BDA0002803808720000055
Figure BDA0002803808720000056
Alternatively, the plasma light absorber may be
Figure BDA0002803808720000061
The photoacid generator can be
Figure BDA0002803808720000062
Alternatively, the plasma light absorber may be
Figure BDA0002803808720000063
The photoacid generator can be
Figure BDA0002803808720000064
Alternatively, the plasma light absorber may be
Figure BDA0002803808720000065
The photoacid generator can be
Figure BDA0002803808720000066
Alternatively, the plasma light absorber may be
Figure BDA0002803808720000067
The photoacid generator can be
Figure BDA0002803808720000068
Photosensitive polymer
The photopolymer may be a polymer that is capable of undergoing a photochemical reaction with Deep Ultraviolet (DUV) light. For example, the photosensitive polymer may be a polymer that chemically reacts when a photoacid generator (PAG) mixed with the photosensitive polymer is exposed to light such as deep ultraviolet light to generate an acid, and the acid thus generated chemically reacts the polymer to thereby make the polymer increase its hydrophilicity or hydrophobicity. It should be appreciated that the photopolymer need not be directly sensitive to light (e.g., exposure of the photopolymer to light need not change the chemical composition of the photopolymer, although the chemical composition of the photopolymer can change due to the acid generated by the exposed PAG mixed with the photopolymer). In some embodiments, the solubility of the photopolymer in the base can be increased due to a photochemical reaction. In some embodiments, the photopolymer may have a structure in which a protecting group is bonded to the repeating unit, and the protecting group may be deprotected during exposure so that the photopolymer is well soluble in a base. The photoresist may be a positive tone photoresist in which portions of the photoresist removed by subsequent photoresist development are exposed to light (e.g., DUV light). Deprotected protecting groups can produce new acids for chemical amplification.
In one embodiment of the photoresist composition, the photosensitive polymer may be a phenolic resin, a polyhydroxystyrene resin, an acrylic resin, or a combination thereof.
The phenolic resin may be a resin having a repeating unit represented by formula (IV),
Figure BDA0002803808720000071
in the formula (IV), R5aIs a protecting group which is cleaved by an acid, and R5bAnd R5cEach of which is a hydrogen atom or C1-C6An alkyl group. R5aIs C1-C6Linear, branched or cyclic alkyl, vinyloxyethyl, tetrahydropyranyl, tetrahydrofuranyl, trialkylsilyl, isohampanyl, 2-methyl-2-adamantyl, 2-ethyl-2-adamantyl, 3-tetrahydrofuranyl, 3-oxocyclohexyl, γ -butyrolactone-3-yl, mevalonolactone, γ -butyrolactone-2-yl, 3-methyl- γ -butyrolactone-3-yl, 2-tetrahydropyranyl, 2-tetrahydrofuranyl, 2, 3-propylenecarbonate-1-yl, 1-methoxyethyl, 1-ethoxyethyl, 1- (2-methoxyethoxy) ethyl, 1- (2-acetoxyethoxy) ethyl, isopropylbenzyl, and isopropylbenzyl, Tert-butoxycarbonylmethyl, methoxymethyl, ethoxymethyl, trimethoxysilyl or triethoxysilyl, and may be methoxyethyl, ethoxyethyl, n-propoxyethyl, isopropoxyethyl, n-butoxyethyl, isobutoxyethyl, tert-butoxyethyl, cyclohexyloxyethyl, methoxypropyl, ethoxypropyl, 1-methoxy-1-methyl-ethyl, 1-ethoxy-1-methylethyl, tert-butoxycarbonyl (t-BOC) or tert-butoxycarbonylmethyl. The linear or branched alkyl group may include, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, isopentyl, or neopentyl. The cyclic alkyl group may include, for example, a cyclopentyl group or a cyclohexyl group.
The polyhydroxystyrene resin may be a resin having a repeating unit represented by formula (V),
Figure BDA0002803808720000081
in the formula (V), R7aIs a hydrogen atom or C1-6Alkyl, and R7bIs an acid-cleavable protecting group. The acid-cleavable protecting group is as defined above.
The polyhydroxystyrene resin may include another polymerizable compound as a repeating unit. Examples of the polymerizable compound may include, but are not limited to: monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; dicarboxylic acids such as maleic acid, fumaric acid, and itaconic acid; methacrylic acid derivatives having a carboxyl group and an ester bond, such as 2-methacryloyloxyethylsuccinic acid, 2-methacryloyloxyethylmaleic acid, 2-methacryloyloxyethylphthalic acid and 2-methacryloyloxyethylhexahydrophthalic acid; alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, and butyl (meth) acrylate; hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate; aryl (meth) acrylates such as phenyl (meth) acrylate and benzyl (meth) acrylate; dicarboxylic acid diesters such as diethyl maleate and dibutyl fumarate; vinyl-containing aromatic compounds such as styrene, α -methylstyrene, chlorostyrene, chloromethylstyrene, vinyltoluene, hydroxystyrene, α -methylhydroxystyrene and α -ethylhydroxystyrene; vinyl group-containing aliphatic compounds such as vinyl acetate; conjugated dienes such as butadiene and isoprene; nitrile group-containing polymerizable compounds such as acrylonitrile and methacrylonitrile; chlorine-containing polymerizable compounds such as vinyl chloride and vinylidene chloride; and amide bond-containing polymerizable compounds such as acrylamide and methacrylamide.
The acrylic resin may be a resin having a repeating unit represented by formula (VI).
Figure BDA0002803808720000082
In the formula (VI), R8aIs a hydrogen atom, C1-C6Straight or branched alkyl, fluorine atom or C1-C6A linear or branched fluorinated alkyl group, and R8bIs an acid-cleavable protecting group. The acid-cleavable protecting group is as defined above.
In a certain embodiment of the photoresist composition, the photosensitive polymer may include a (meth) acrylate-based polymer. The (meth) acrylate-based polymer may be an aliphatic (meth) acrylate-based polymer, and may include, for example, polymethyl methacrylate (PMMA), poly (t-butyl methacrylate), poly (methacrylic acid), poly (norbornyl methacrylate), binary or ternary copolymers of the repeating units of the above (meth) acrylate-based polymers, or combinations thereof.
The acrylic resin may include another polymerizable compound as a repeating unit. Examples of the polymerizable compound may include, but are not limited to: acrylic esters having an ether bond such as 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, methoxytriethylene glycol (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethylcarbitol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, and tetrahydrofurfuryl (meth) acrylate; monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; dicarboxylic acids such as maleic acid, fumaric acid, and itaconic acid; methacrylic acid derivatives having a carboxyl group and an ester bond, such as 2-methacryloyloxyethylsuccinic acid, 2-methacryloyloxyethylmaleic acid, 2-methacryloyloxyethylphthalic acid and 2-methacryloyloxyethylhexahydrophthalic acid; alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and cyclohexyl (meth) acrylate; hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate; aryl (meth) acrylates such as phenyl (meth) acrylate and benzyl (meth) acrylate; dicarboxylic acid diesters such as diethyl maleate and dibutyl fumarate; vinyl-containing aromatic compounds such as styrene, α -methylstyrene, chlorostyrene, chloromethylstyrene, vinyltoluene, hydroxystyrene, α -methylhydroxystyrene and α -ethylhydroxystyrene; vinyl group-containing aliphatic compounds such as vinyl acetate; conjugated dienes such as butadiene and isoprene; nitrile group-containing polymerizable compounds such as acrylonitrile and methacrylonitrile; chlorine-containing polymerizable compounds such as vinyl chloride and vinylidene chloride; and amide bond-containing polymerizable compounds such as acrylamide and methacrylamide.
In one embodiment of the photoresist composition, the photosensitive polymer can have the following structure:
Figure BDA0002803808720000091
wherein x1:y1:z1＝66.5:8.5:25。
The photosensitive polymer may be obtained by addition polymerization of polymer monomers, which is conventional in the art. In one embodiment of the photoresist composition, the photosensitive polymer can be obtained by addition polymerization of monomer A, monomer B, and monomer C, wherein the molar ratio of monomer A, monomer B, and monomer C is 66.5:8.5:25,
Figure BDA0002803808720000092
in a certain embodiment of the photoresist composition, the weight average molecular weight (Mw) of the photosensitive polymer may be 10,000 to 600,000; e.g., 20,000 to 400,000; and for example 22,000. Among them, the Mw value may be a value measured using Gel Permeation Chromatography (GPC) by setting polystyrene as a standard.
In a certain embodiment of the photoresist composition, the photopolymer can have a polydispersity index (PDI) of 1 to 3, such as 2.1.
In one embodiment of the photoresist composition, the amount of the photopolymer can be a level conventional to photoresists used in the art, for example, the photopolymer can be present in a mass fraction of 5 wt% to 60 wt% (e.g., 20 wt% to 40 wt%, again e.g., 30 wt%) of the total mass of the feedstock with respect to the mass of the photopolymer.
Organic solvent
In one embodiment of the photoresist composition, the organic solvent may be any organic solvent conventional in the art, including, but not limited to: ketones (such as acetone, methyl ethyl ketone, cyclohexanone, methyl isoamyl ketone and 2-heptanone), polyols and derivatives thereof (such as monomethyl, monoethyl, monopropyl, monobutyl and monophenyl ethers of ethylene glycol, ethylene glycol monoacetate, diethylene glycol monoacetate, propylene glycol methyl ether acetate, propylene glycol monoacetate, dipropylene glycol and dipropylene glycol monoacetate), cyclic ethers (such as dioxane), esters (such as ethyl formate, methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, methyl acetoacetate, ethyl pyruvate, ethyl ethoxyacetate, methyl methoxypropionate, ethyl ethoxypropionate, methyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate), Methyl 2-hydroxy-3-methylbutyrate, 3-methoxybutyl acetate, and 3-methyl-3-methoxybutyl acetate), aromatic hydrocarbons (such as toluene and xylene), or combinations thereof.
In one embodiment of the photoresist composition, the organic solvent may be propylene glycol methyl ether and/or propylene glycol methyl ether acetate, and when the organic solvent is propylene glycol methyl ether and propylene glycol methyl ether acetate, the volume ratio of the propylene glycol methyl ether and the propylene glycol methyl ether acetate may be 5:1 to 2:1, for example, 4: 1.
In one embodiment of the photoresist composition, the organic solvent can be present in an amount conventional to photoresists used in the art, for example, in a mass fraction of 20 wt% to 80 wt% (e.g., 40 wt% to 70 wt%, and again, e.g., 60 wt%) of the photosensitive polymer as a percentage of the total mass of the starting materials.
Other Components
In one embodiment of the photoresist composition, the photoresist composition may further comprise other components that are conventionally added to photoresists in the art, such as leveling agents, surfactants, adhesion promoters, quenchers, crosslinkers, and the like.
In a certain embodiment of the photoresist composition, the leveling agent and surfactant may be leveling agents and surfactants conventionally used in the art, and examples thereof may include, but are not limited to: fluoroalkyl benzene sulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkyl ammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglyceryl tetrakis (fluoroalkyl polyoxyethylene ether), fluoroalkyl trimethyl ammonium salt, fluoroalkyl sulfamate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene tridecyl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, fluoroalkyl ammonium sulfate, fluoroalkyl ammonium salt, fluoroalkyl, Polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkyl benzene sulfonate, alkyl diphenyl ether disulfonate, or combinations thereof.
In a certain embodiment of the photoresist composition, the content of the leveling agent or surfactant may be a conventional content used in photoresists in the art, for example, the content of the leveling agent or surfactant may be 0.001 wt% to 0.1 wt% each in terms of mass fraction, which is a percentage of the mass of the leveling agent or surfactant to the total mass of the raw materials.
In a certain embodiment of the photoresist composition, the adhesion promoter may be one conventionally used in the art for enhancing adhesion to a substrate. The adhesion promoter may include, but is not limited to, silane-based, aluminum-based, or titanate-based compounds. Specifically, the adhesion promoter may include, for example, 3-glycidoxypropyldimethylethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltrimethoxysilane, aluminum acetylalkoxydiisopropoxide, tetraisopropylbis (dioctylphosphite) titanate, or a combination thereof.
In one embodiment of the photoresist composition, the adhesion promoter may be present in an amount conventional to photoresists of the art, for example, in a mass fraction of 0.1 wt% to about 10 wt%, the mass fraction being the mass of the adhesion promoter as a percentage of the total mass of the feedstock.
In a certain embodiment of the photoresist composition, the quencher may be a quencher conventionally used in the art for adjusting the diffusion rate of a material such as a generated acid, and examples thereof may include, but are not limited to: a primary, secondary or tertiary amine compound, and more particularly, an amine compound having a hydroxyl group, an ether bond, an ester bond, a lactone ring, a cyano group or a sulfonate ester bond, or an amine compound obtained by protecting a primary or secondary amine with a carbamate group; salts, such as sulfonium, iodonium or ammonium salts of carboxylic acids; or a combination thereof.
In one embodiment of the photoresist composition, the quencher can be present in an amount conventional to photoresists used in the art, for example, the quencher can be present in an amount of 0.01 wt% to 5 wt% by mass fraction as a percentage of the mass of the quencher to the total mass of the starting materials.
In a certain embodiment of the photoresist composition, the crosslinking agent may be one conventionally used in the art, and examples thereof may include, but are not limited to: a nitrogen-containing compound having at least two crosslinking substituents (e.g., hydroxymethyl, methoxymethyl, or butoxymethyl). Specifically, the crosslinking agent may include, for example, hexamethoxymethylmelamine, tetramethoxymethylbenzoguanamine, 1,3,4, 6-tetrakis (methoxymethyl) glycoluril, 1,3,4, 6-tetrakis (butoxymethyl) glycoluril, 1,3,4, 6-tetrakis (hydroxymethyl) glycoluril, 1, 3-bis (hydroxymethyl) urea, 1,3, 3-tetrakis (butoxymethyl) urea, 1,3, 3-tetrakis (methoxymethyl) urea, or a combination thereof.
In one embodiment of the photoresist composition, the crosslinker may be present in an amount conventional to photoresists used in the art, for example, in a mass fraction of 0.01 wt% to 5 wt%, the mass fraction being the mass of the crosslinker as a percentage of the total mass of the starting materials.
In one embodiment of the photoresist composition, the photoresist composition may further comprise other components; for example salicylic acid and/or triethylamine, wherein the salicylic acid may be present in an amount of 0.1 wt% to 10 wt% (e.g. 1 wt% to 5 wt%, again e.g. 2 wt%) based on the mass fraction, which is the mass of each component as a percentage of the total mass of the feedstock, and the triethylamine may be present in an amount of 0.1 wt% to 10 wt% (e.g. 1 wt% to 5 wt%, again e.g. 2 wt%).
In another aspect, the present invention also provides the use of an acylphosphine oxide compound of formula (I) as described above as a plasma light absorber in a KrF thick film photoresist.
In another aspect, the present invention also provides a use of the above photoresist composition in the manufacture of a semiconductor device.
In one embodiment of the application, the method of manufacturing a semiconductor device includes: forming a target layer on a substrate, the target layer including at least one dielectric layer, forming a layer of the above-described photoresist composition for Deep Ultraviolet (DUV) light on the target layer, selectively exposing the layer of the photoresist composition for DUV light to krypton fluoride (KrF) laser through a photomask, forming a photoresist pattern by developing the exposed layer of the photoresist composition, and patterning the substrate in a plasma environment using the photoresist pattern as an etch mask.
The above preferred conditions can be arbitrarily combined to obtain preferred embodiments of the present invention without departing from the common general knowledge in the art.
The reagents and starting materials used in the present invention are commercially available.
The positive progress effects of the invention are as follows: the acylphosphine oxide compound in the photoresist composition provided by the invention is used as a plasma light absorber and is cooperated with a conventional photoacid generator to generate better light transmittance, so that the photoresist composition provided by the invention can form a photoresist pattern which has a large thickness (for example, 2.5-25 μm, for example, 10 μm) and can realize high-quality etching of a lower layer when being used together with Deep Ultraviolet (DUV) light.
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions.
In the following examples, acylphosphine oxide compounds as plasma light absorbers, for example, compound 1-A or compound 1-B, are commercially available or can be prepared by the method disclosed in patent CN 101065388A.
Figure BDA0002803808720000131
In the following examples, the photosensitive polymer may be prepared by reacting monomer A
Figure BDA0002803808720000132
Monomer B
Figure BDA0002803808720000133
And monomer C
Figure BDA0002803808720000134
The addition polymerization reaction is carried out, wherein the molar ratio of the monomer A to the monomer B to the monomer C is 66.5:8.5: 25. The structural formula of the finally prepared photosensitive polymer is as follows:
Figure BDA0002803808720000135
wherein x1:y1:z166.5:8.5: 25; a weight average molecular weight (Mw) of 22,000; the polydispersity index (PDI) is 2.1.
Examples 1 to 6 and comparative examples 1 to 3
The preparation method of the photoresist composition comprises the following steps:
mixing 1 wt% of a plasma light absorber, 5 wt% of a photoacid generator, 30 wt% of a photopolymer, 60 wt% of an organic solvent, 2 wt% of triethylamine, and 2 wt% of salicylic acid at room temperature to obtain photoresist compositions 1 to 6 and comparative photoresist compositions 1 to 3, wherein the plasma light absorber and the photoacid generator in examples 1 to 6 and comparative examples 1 to 3 are shown in table 1;
the photosensitive polymer is
Figure BDA0002803808720000136
(x1:y1:z1＝66.5:8.5:25)；
The organic solvent is propylene glycol methyl ether and propylene glycol methyl ether acetate (v/v ═ 4: 1).
With reference to the preparation method described in example 1 of patent TW200741355A, photoresist compositions 1-6 and comparative photoresist compositions 1-3 were formed into photoresist masks.
Table 1: species of plasma light absorber and photoacid generator in raw material of photoresist
Figure BDA0002803808720000141
The thickness of the resist film (nm) at the measurement point of the wafer 49 was measured by using a nano-meter tester (manufactured by Nanometrics corporation) and was 10 μm.
Effects of the embodiment
The photo-resist masks prepared in examples 1 to 6 and comparative examples 1 to 3 were measured for their absorbance of light at a wavelength of 248nm (UV)248nm) And absorbance of light at 300nm wavelength (UV)300nm). The results are shown in table 2 below.
Table 2: practice ofUV of Photoresist masks of examples 1-6 and comparative examples 1-3248nm/UV300nmValue of
Figure BDA0002803808720000142
The above results show that examples 1 to 6 of the present invention have high transmittance to light in the wavelength band of 200nm to 280nm (e.g., 248nm), which may be useful for an exposure process using Deep Ultraviolet (DUV) light, and that compared to the prior art in which a phenol compound having an electron donating substituent at the ortho-position of a hydroxyl group and an electron withdrawing substituent at the para-position or meta-position thereof is used as a plasma light absorber, the acylphosphine oxide compound in the photoresist composition of the present invention can cooperate with a conventional photoacid generator (e.g., triphenylsulfonium) to produce better light transmittance, so that the photoresist composition of the present invention can form a photoresist pattern having a large thickness and capable of achieving high-quality etching of the lower layer when used together with Deep Ultraviolet (DUV) light.

Claims (11)

1. A photoresist composition characterized by being prepared from the following raw materials: plasma light absorbers, photoacid generators, photosensitive polymers, and organic solvents; wherein the plasma light absorber is an acylphosphine oxide compound shown in formula (I),
Figure FDA0002803808710000011
wherein m is 1 or 2;
x is oxygen or sulfur;
R1and R3Are each independently C1-4Alkyl, phenyl, -C (O) -phenyl, C (O) -phenyl1-4Phenyl substituted by alkyl, or by C1-4Alkyl-substituted-c (o) -phenyl;
R2is C1-4Alkyl, phenyl, or by C1-4Alkyl-substituted phenyl;
and R is1、R2And R3Is differentWhen is C1-4An alkyl group.
2. The photoresist composition of claim 1, wherein in the acylphosphine oxide compound of formula (I), m, R1、R2And R3As defined in one of (a) - (e):
(a) m is 1, R1And R3Is phenyl, R2Is a quilt C1-4Alkyl-substituted phenyl;
(b) m is 1, R1And R3One of which is phenyl and the other is C1-4alkyl-substituted-C (O) -phenyl, R2Is C1-4An alkyl group;
(c) m is 2, R1Is phenyl, R2Is a quilt C1-4Alkyl-substituted phenyl, R3Is absent;
(d) m is 2, R1Is a quilt C1-4alkyl-substituted-C (O) -phenyl, R2Is a quilt C1-4Alkyl-substituted phenyl, R3Is absent; or
(e) m is 2, R1Is phenyl; r2Is C1-4Alkyl radical, R3Is absent.
3. The photoresist composition of claim 1 or 2,
in the acyl phosphine oxide compound shown in the formula (I), X is oxygen;
and/or, in the acylphosphine oxide compound shown in the formula (I), R1、R2And R3C as described in (1)1-4Alkyl is tert-butyl;
and/or, in the acylphosphine oxide compound shown in the formula (I), R1、R2And R3The quilt of (1)1-4Alkyl-substituted phenyl is
Figure FDA0002803808710000012
For example,
Figure FDA0002803808710000013
and/or, in the acylphosphine oxide compound shown in the formula (I), R1And R3The quilt of (1)1-4alkyl-substituted-C (O) -phenyl is
Figure FDA0002803808710000021
4. The photoresist composition of any one of claims 1 to 3,
the positive ions of the photoacid generator are phenyl sulfonium positive ions shown in a formula (II) and/or phenyl iodonium positive ions shown in a formula (III),
Figure FDA0002803808710000022
wherein R is3And R4Independently is phenyl, carboxy, -C1-60alkylene-COOH, RaSubstituted or unsubstituted C1-60Alkyl radical, RaSubstituted or unsubstituted C1-60Alkoxy radical, RaSubstituted or unsubstituted C2-60Alkenyl radical, RaSubstituted or unsubstituted C2-60Alkynyl, or RaSubstituted or unsubstituted C3-60A cycloalkyl group; raIndependently is C1-6Alkyl radical, C1-6Alkoxy radical, C6-12Aromatic ring, halogen atom, OH, NH2An aldehyde group or a carboxyl group;
and/or, the anion of the photoacid generator is a non-nucleophilic anion; for example, the anion may be a halide ion, (R)7(SO2))(R8(SO2))N-、(R7(SO2))(R8(SO2))(R9(SO2))C-Or R10(SO3)-(ii) a Wherein R is7、R8、R9Each independently of the other being completely fluorinated C2-4Alkyl, completely fluorinated phenyl, -phenyl- (completely fluorinated or unsubstituted C2-46Alkyl), - (C)Completely fluorinated C2-4Alkylene) -O-completely fluorinated C2-C4Alkyl, - (completely fluorinated C)2-4Alkylene) -a completely fluorinated 6-membered heterocycle containing 1 oxygen atom, or- (C)1-3Alkylene) - (a 7-to 10-membered bridged ring containing a C ═ O group); or, R7、R8Is connected to contain- (SO)2)N-(SO2) -a fully fluorinated 6-8 membered heterocyclic ring; r10Is completely fluorinated or unsubstituted C6-10Aryl or completely fluorinated or unsubstituted C1-10An alkyl group.
5. The photoresist composition of any one of claims 1 to 4,
the cation of the photoacid generator is
Figure FDA0002803808710000023
For example,
Figure FDA0002803808710000024
and/or the anion of the photoacid generator is a trifluoromethanesulfonate ion.
6. The photoresist composition of any one of claims 1 to 5,
the acyl phosphine oxide compound shown in the formula (I) is:
Figure FDA0002803808710000031
Figure FDA0002803808710000032
Figure FDA0002803808710000033
for example,
Figure FDA0002803808710000034
and/or, the lightThe antacid is
Figure FDA0002803808710000035
For example,
Figure FDA0002803808710000036
7. the photoresist composition of any one of claims 1 to 6,
the plasma light absorber is
Figure FDA0002803808710000037
And the photoacid generator is
Figure FDA0002803808710000038
Alternatively, the plasma light absorber is
Figure FDA0002803808710000041
And the photoacid generator is
Figure FDA0002803808710000042
Alternatively, the plasma light absorber is
Figure FDA0002803808710000043
And the photoacid generator is
Figure FDA0002803808710000044
Alternatively, the plasma light absorber is
Figure FDA0002803808710000045
And the photoacid generator is
Figure FDA0002803808710000046
Alternatively, the plasma light absorber is
Figure FDA0002803808710000047
And the photoacid generator is
Figure FDA0002803808710000048
8. The photoresist composition of any one of claims 1 to 7,
the photosensitive polymer is phenolic resin, polyhydroxystyrene resin, acrylic resin or a combination thereof; for example, the photosensitive polymer can be obtained by addition polymerization of a monomer A, a monomer B and a monomer C, wherein the molar ratio of the monomer A, the monomer B and the monomer C is 66.5:8.5:25,
Figure FDA0002803808710000051
and/or the organic solvent is a ketone, a polyol and derivatives thereof, a cyclic ether, an ester, an aromatic hydrocarbon, or combinations thereof; for example, the organic solvent is propylene glycol methyl ether and/or propylene glycol methyl ether acetate, and when the organic solvent is propylene glycol methyl ether and propylene glycol methyl ether acetate, the volume ratio of the propylene glycol methyl ether to the propylene glycol methyl ether acetate is 5: 1-2: 1; e.g., 4: 1;
and/or, the content of the plasma light absorber is 0.5 wt% to 2 wt% in terms of mass fraction; for example 0.7 wt% to 1.3 wt%; and also for example 1 wt%;
and/or, the photoacid generator is present in an amount of 1 wt% to 10 wt% in terms of mass fraction; e.g., 3 wt% to 8 wt%; and also for example 5 wt%;
and/or, the content of the photosensitive polymer is 5 wt% to 60 wt% in terms of mass fraction; e.g., 20 wt% to 40 wt%; as another example 30 wt%;
and/or, the content of the organic solvent is 20 wt% to 80 wt% in terms of mass fraction; e.g., 20 wt% to 70 wt%; as another example 60 wt%;
the mass fraction is the percentage of the mass of each component in the total mass of the raw materials.
9. The photoresist composition of any one of claims 1 to 8, further comprising other components, wherein the other components are salicylic acid and/or triethylamine, wherein the salicylic acid can be present in an amount of 0.1 wt% to 10 wt%; e.g., 1 wt% to 5 wt%; for another example, 2 wt%, the triethylamine may be present in an amount of 0.1 wt% to 10 wt%; e.g., 1 wt% to 5 wt%; for another example, 2 wt%, the mass fraction being the mass of each component as a percentage of the total mass of the raw material.
10. An application of acylphosphine oxide compound shown in formula (I) as a plasma light absorber in KrF thick film photoresist,
Figure FDA0002803808710000052
wherein m is 1 or 2;
x is oxygen or sulfur;
R1and R3Are each independently C1-4Alkyl, phenyl, -C (O) -phenyl, C (O) -phenyl1-4Phenyl substituted by alkyl, or by C1-4Alkyl-substituted-c (o) -phenyl;
R2is C1-4Alkyl, phenyl, or by C1-4Alkyl-substituted phenyl;
and R is1、R2And R3Is not simultaneously C1-4An alkyl group.
11. Use of a photoresist composition as claimed in any one of claims 1 to 9 in the manufacture of a semiconductor device.
CN202011360612.3A 2020-11-27 2020-11-27 KrF thick film photoresist additive and photoresist composition containing same Pending CN112485963A (en)

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US6042988A (en) * 1996-12-26 2000-03-28 Tokyo Ohka Kogyo Co., Ltd. Chemical-amplification-type negative resist composition
JP2011038014A (en) * 2009-08-13 2011-02-24 Sumitomo Seika Chem Co Ltd Photoacid generator and photoreactive composition
CN103073658A (en) * 2011-10-26 2013-05-01 深圳市有为化学技术有限公司 Photoinitiator mixture of novel aromatic hydroxyl ketone and acylphosphine oxide, and composite system of photoinitiator mixture and photoabsorber
CN103415540A (en) * 2011-03-07 2013-11-27 三洋化成工业株式会社 Photosensitive composition, cured article, and method for producing actinically cured article
CN108586304A (en) * 2012-10-26 2018-09-28 罗门哈斯电子材料有限公司 Photo-induced acid compound and photo-corrosion-resisting agent composition comprising it, include the coating product and its manufacturing method of photoresist
CN109581810A (en) * 2017-09-29 2019-04-05 三星电子株式会社 The method of photoetching compositions and manufacturing semiconductor devices for deep ultraviolet light
CN111694215A (en) * 2019-03-14 2020-09-22 常州强力先端电子材料有限公司 Photoresist composition and method for forming photolithographic pattern

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6042988A (en) * 1996-12-26 2000-03-28 Tokyo Ohka Kogyo Co., Ltd. Chemical-amplification-type negative resist composition
JP2011038014A (en) * 2009-08-13 2011-02-24 Sumitomo Seika Chem Co Ltd Photoacid generator and photoreactive composition
CN103415540A (en) * 2011-03-07 2013-11-27 三洋化成工业株式会社 Photosensitive composition, cured article, and method for producing actinically cured article
CN103073658A (en) * 2011-10-26 2013-05-01 深圳市有为化学技术有限公司 Photoinitiator mixture of novel aromatic hydroxyl ketone and acylphosphine oxide, and composite system of photoinitiator mixture and photoabsorber
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