CN107340687B - Composition for hard mask - Google Patents

Composition for hard mask Download PDF

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CN107340687B
CN107340687B CN201710220902.XA CN201710220902A CN107340687B CN 107340687 B CN107340687 B CN 107340687B CN 201710220902 A CN201710220902 A CN 201710220902A CN 107340687 B CN107340687 B CN 107340687B
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carbon atoms
independently
group
aryl group
compound
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CN107340687A (en
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崔汉永
梁敦植
金相泰
成始震
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Dongwoo Fine Chem Co Ltd
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/09Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/26Polyhydroxylic alcohols containing only six-membered aromatic rings as cyclic part
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/0048Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents

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Abstract

The present invention relates to a composition for a hard mask, and more particularly, to a composition for a hard mask, which can form an underlayer film (hard mask) having excellent heat resistance by including a compound having two or more tertiary alcohol groups in a molecule and a solvent.

Description

Composition for hard mask
Technical Field
The present invention relates to a composition for a hard mask.
Background
In the microelectronics industry and in the industrial fields of microstructures (e.g., micromachines, magnetoresistive heads, etc.), etc., there is a continuing demand to reduce the size of the structural shapes. Furthermore, in the microelectronics industry, there are requirements for: the size of microelectronic devices is reduced to provide more circuitry for a given chip size.
To reduce the size of the shapes, efficient photolithography is essential.
In a typical photolithography process, a resist is first applied to an underlying material, and then exposed to radiation to form a resist layer. Next, the resist layer is developed with a developer to form a patterned resist layer, and the substance present in the openings of the patterned resist layer is etched to transfer the pattern to the underlying material. After the transfer is finished, the following processes are carried out: the photosensitive resist is exposed pattern-wise to form a patterned resist layer. The image is then developed by contacting the exposed resist layer with an optional substance, typically an aqueous alkaline developer. Next, the substance present in the openings of the patterned resist layer is etched, whereby the pattern is transferred to the underlying material. After the transfer, the remaining resist layer is removed.
In order to minimize the reflectivity between the resist layer and the underlying material, most of the above-described photolithography processes use an anti-reflective coating (ARC) to increase resolution. However, in the step of etching the antireflective coating after patterning, the resist layer is also consumed in a large amount, and there is a possibility that additional patterning is necessary in the subsequent etching step.
In other words, in some cases, the resist used in the lithographic imaging process may not have sufficient resistance to the etching step to the extent that the desired pattern is efficiently transferred to the underlying material. Therefore, in the case of an ultra-thin film resist layer in which a resist material needs to be used extremely thinly, in the case of a substrate to be etched thick, in the case of a substrate requiring a deep etching depth, in the case of a predetermined underlayer material requiring a specific etchant (etchant), or the like, a resist underlayer film is used.
The resist underlayer film serves as an intermediate layer between the resist layer and an underlayer material that can be patterned by transfer from the patterned resist, and needs to withstand an etching step required for receiving a pattern from the patterned resist layer and transferring the pattern to the underlayer material.
In order to form such an underlayer film, many materials have been tried, but improvements in the composition of the underlayer film are still continuously demanded.
Conventionally, materials for forming an underlayer film are difficult to apply to a substrate, and therefore, they have been subjected to chemical or physical vapor deposition, special solvents, or high-temperature firing, for example, but they have a problem of high cost. In view of this, studies have been made in recent years on a composition for an underlayer film that can be applied by a spin coating method without performing high-temperature baking.
In addition, studies were conducted on the following lower layer film composition: the resist layer formed on the upper portion can be easily selectively etched using the resist layer as a mask, and particularly, when the lower layer is a metal layer, the resist film has resistance to an etching process required for patterning the lower layer using the lower layer film as a mask.
Korean laid-open patent No. 10-2010-0082844 discloses a technique concerning a resist underlayer film forming composition.
Documents of the prior art
Patent document
Korean laid-open patent No. 10-2010-0082844
Disclosure of Invention
Problems to be solved
The purpose of the present invention is to provide a composition for a hard mask, which is capable of forming a resist underlayer film (hard mask) having excellent heat resistance.
Means for solving the problems
1. A hardmask composition comprising a compound having two or more tertiary alcohol groups in a molecule and a solvent.
2. The hardmask composition according to claim 1, wherein the compound is at least one selected from the group consisting of compounds represented by the following chemical formulae 1 to 3:
[ chemical formula 1]
Figure BDA0001263713510000031
(wherein n is 1 to 10,
R1and R2Each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Ar1each independently an arylene group having 6 to 20 carbon atoms,
Ar2and Ar3Each independently an aryl group having 6 to 20 carbon atoms,
ar above1、Ar2、Ar3、R1And R2Can be independently substituted by-OH, -ORa、-OAra、-Ra、-AraFurther substituted, above-RaAn aliphatic hydrocarbon group having 1 to 6 carbon atoms, the above-mentioned-AraIs an aryl group having 6 to 20 carbon atoms)
[ chemical formula 2]
Figure BDA0001263713510000032
(wherein n is 2 to 10,
R3each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Ar4an aryl group having 6 to 20 carbon atoms wherein n hydrogen atoms may be substituted,
Ar5each independentlyAn aryl group having 6 to 20 carbon atoms,
r is as defined above3、Ar4And Ar5Can be independently substituted by-OH, -ORa、-OAra、-Ra、-AraFurther substituted, above-RaAn aliphatic hydrocarbon group having 1 to 6 carbon atoms, the above-mentioned-AraIs an aryl group having 6 to 20 carbon atoms)
[ chemical formula 3]
Figure BDA0001263713510000041
(in the formula, R4And R5Each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Ar6and Ar7Each independently an arylene group having 6 to 20 carbon atoms,
r is as defined above4、R5、Ar6And Ar7Can be independently substituted by-OH, -ORa、-OAra、-Ra、-AraFurther substituted, above-RaAn aliphatic hydrocarbon group having 1 to 6 carbon atoms, the above-mentioned-AraIs an aryl group having 6 to 20 carbon atoms.
3. The hardmask composition according to claim 2, wherein Ar is1、Ar6And Ar7Each independently is phenylene, naphthalene diyl, anthracene diyl, stilbene diyl, or pyrenediyl.
4. The hardmask composition according to claim 2, wherein Ar is2、Ar3And Ar5Each independently is phenyl, naphthyl, anthryl, stilbenyl or pyrenyl.
5. The hardmask composition according to claim 2, wherein Ar is4Is phenyl, naphthyl, anthryl, stilbenyl or pyrenyl.
6. The hardmask composition according to claim 2, wherein R is1~R5Each independently being methyl, vinyl, allyl or phenyl.
7. The hardmask composition according to claim 1, wherein the composition comprises 10 to 70 wt% of the compound and 30 to 90 wt% of the solvent, based on the total weight of the composition.
8. The hardmask composition according to claim 1, further comprising at least one of a crosslinking agent and a catalyst.
Effects of the invention
The composition for a hard mask of the present invention can form a polymer for a resist underlayer film having excellent heat resistance by improving the crosslinkability and suppressing excessive progress of a crosslinking reaction.
In addition, the composition for a hard mask according to one embodiment of the present invention can form a polymer for a resist underlayer film having excellent etching selectivity by increasing the carbon content (C%) in the compound.
Detailed Description
One embodiment of the present invention relates to a composition for a hard mask, which comprises a compound having two or more tertiary alcohol groups in a molecule and a solvent, and can form a resist underlayer film (hard mask) having excellent heat resistance.
Hereinafter, specific embodiments of the present invention will be described. However, this is merely an example, and the present invention is not limited thereto.
In the present invention, when there are isomers of the compound or resin represented by the formula, the corresponding compound or resin represented by the formula means a representative formula including the isomers thereof.
<Composition for hard mask>
The composition for a hard mask of the present invention comprises a compound (A) having two or more tertiary alcohol groups in a molecule and a solvent (B).
Compound (A)
The present invention can provide a hard mask formed from the composition for a hard mask of the present invention, which has excellent heat resistance, by including the compound (a).
Specifically, since the compound (a) contains two or more tertiary alcohol groups in the molecule and such tertiary alcohol groups are more likely to react with Sn1 than secondary alcohol groups or primary alcohol groups, the crosslinking property can be improved and the heat resistance can be improved when a hard mask is produced from the hard mask composition. In addition, the tertiary alcohol suppresses excessive progress of the crosslinking reaction and is also insensitive to the oxidation reaction, and thus, in the case of being used for manufacturing a hard mask, the heat resistance of the manufactured hard mask is improved.
In addition, in the present invention, by including the compound (a), the etching resistance (etching selectivity) to the halogen gas can be improved due to a high carbon content (C%) in the compound.
In view of this, for example, the compound (a) may be at least one selected from the group consisting of compounds represented by the following chemical formulae 1 to 3:
[ chemical formula 1]
Figure BDA0001263713510000051
(wherein n is 1 to 10,
R1and R2Each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Ar1each independently an arylene group having 6 to 20 carbon atoms,
Ar2and Ar3Each independently an aryl group having 6 to 20 carbon atoms,
ar above1、Ar2、Ar3、R1And R2Can be independently substituted by-OH, -ORa、-OAra、-Ra、-AraFurther substituted, above-RaAn aliphatic hydrocarbon group having 1 to 6 carbon atoms, the above-mentioned-AraIs an aryl group having 6 to 20 carbon atoms)
[ chemical formula 2]
Figure BDA0001263713510000061
(wherein n is 2 to 10,
R3each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Ar4an aryl group having 6 to 20 carbon atoms wherein n hydrogen atoms may be substituted,
Ar5each independently an aryl group having 6 to 20 carbon atoms,
r is as defined above3、Ar4And Ar5Can be independently substituted by-OH, -ORa、-OAra、-Ra、-AraFurther substituted, above-RaAn aliphatic hydrocarbon group having 1 to 6 carbon atoms, the above-mentioned-AraIs an aryl group having 6 to 20 carbon atoms)
[ chemical formula 3]
Figure BDA0001263713510000062
(in the formula, R4And R5Each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Ar6and Ar7Each independently an arylene group having 6 to 20 carbon atoms,
r is as defined above4、R5、Ar6And Ar7Can be independently substituted by-OH, -ORa、-OAra、-Ra、-AraFurther substituted, above-RaAn aliphatic hydrocarbon group having 1 to 6 carbon atoms, the above-mentioned-AraAn aryl group having 6 to 20 carbon atoms).
In the formula, "each independently" means that even if a substituent represented by the same symbol in one compound is substituted, if the position thereof is different, other substituents may be substituted. For example, in chemical formula 1, if R2Or Ar1When different repeating units are present in one compound, substituents different from each other may be present within the above-described range.
As mentioned before, due to Ar1~Ar7The polymer for a resist underlayer film has aromatic properties, can further improve crosslinking properties, and can form a polymer for a resist underlayer film having excellent etching selectivity by increasing the carbon content (C%) in the compound.
In the present invention, preferable examples of the aliphatic hydrocarbon group having 1 to 6 carbon atoms include an alkyl group having 1 to 6 carbon atoms, a vinyl group and an allyl group.
In the present invention, Ar is preferred1~Ar7And R1~R5May be as follows.
For example, Ar1、Ar6And Ar7Can be each independently a phenylene group, a naphthalene diyl group, an anthracene diyl group, a stilbene diyl group or a pyrene diyl group,
Ar2、Ar3and Ar5May each independently be phenyl, naphthyl, anthracenyl, stilbenyl or pyrenyl, and furthermore,
Ar4can be phenyl, naphthyl, anthryl, stilbenyl or pyrenyl.
In the present invention, R is preferably1~R5Each independently may be methyl, vinyl, allyl or phenyl, more preferably may be vinyl, allyl or phenyl.
In R according to one embodiment of the invention1~R5When each independently is a vinyl group or an allyl group, the compound (a) has a crosslinkable functional group, and therefore, the heat resistance can be further improved.
In addition, in R according to an embodiment of the present invention1~R5When the phenyl group is contained, since the carbon content (C%) in the compound is significantly increased, a polymer for a resist underlayer film having further improved etching selectivity can be formed.
More preferably, in the hardmask composition according to an embodiment of the present invention, the compound (a) may be at least one selected from the group consisting of the following chemical formulas 11 to 31:
[ chemical formula 11]
Figure BDA0001263713510000081
[ chemical formula 12]
Figure BDA0001263713510000082
[ chemical formula 13]
Figure BDA0001263713510000083
[ chemical formula 14]
Figure BDA0001263713510000084
[ chemical formula 15]
Figure BDA0001263713510000091
[ chemical formula 16]
Figure BDA0001263713510000092
[ chemical formula 17]
Figure BDA0001263713510000093
[ chemical formula 18]
Figure BDA0001263713510000094
[ chemical formula 19]
Figure BDA0001263713510000101
[ chemical formula 20]
Figure BDA0001263713510000102
[ chemical formula 21]
Figure BDA0001263713510000103
[ chemical formula 22]
Figure BDA0001263713510000104
[ chemical formula 23]
Figure BDA0001263713510000111
[ chemical formula 24]
Figure BDA0001263713510000112
[ chemical formula 25]
Figure BDA0001263713510000113
[ chemical formula 26]
Figure BDA0001263713510000114
[ chemical formula 27]
Figure BDA0001263713510000115
[ chemical formula 28]
Figure BDA0001263713510000121
[ chemical formula 29]
Figure BDA0001263713510000122
[ chemical formula 30]
Figure BDA0001263713510000123
For example, the compound (a) according to one embodiment of the present invention can be produced by a grignard reaction in which a ketone is reacted with a grignard reagent. Therefore, the compound (a) according to the present example can be stably produced under mild conditions.
The content of the compound (a) according to an embodiment of the present invention is not particularly limited as long as the object of the present invention can be achieved, and for example, the content may be 10 to 70% by weight based on the total weight of the composition, and when the above range is satisfied, the effect of the present invention can be exhibited most excellently.
Solvent (B)
The solvent according to one embodiment of the present invention is not particularly limited as long as it is an organic solvent having sufficient solubility for the compound (a), and examples thereof include Propylene Glycol Monomethyl Ether Acetate (PGMEA), Propylene Glycol Monomethyl Ether (PGME), cyclohexanone, ethyl lactate, γ -butyrolactone (GBL), acetylacetone (acetyl acetate), and the like, and Propylene Glycol Monomethyl Ether Acetate (PGMEA) is preferable.
The content of the solvent (B) according to one embodiment of the present invention is not particularly limited as long as it can achieve the object of the present invention, and the composition according to the present invention may be contained in the balance other than the reaction components including the compound (a) and other additives. For example, in the case where only the compound (a) is used in the composition, the solvent may be 30 to 90% by weight based on the total weight of the composition, and when the above range is satisfied, the above effects of the present invention can be effectively exhibited.
Crosslinking agent and catalyst
In addition, the composition for a hard mask according to an embodiment of the present invention may further include at least one of a crosslinking agent and a catalyst, as necessary.
The crosslinking agent is not particularly limited as long as it can crosslink the repeating unit of the polymer by heating in a reaction in which a catalytic action is generated by the generated acid, and can react with the hydroxyl group of the compound (a) so as to generate a catalytic action by the generated acid. As a representative example of such a crosslinking agent, any one selected from the group consisting of melamine, amino resin, glycoluril compound, and diepoxy compound can be used.
By further including the above-mentioned crosslinking agent, the curing characteristics of the composition for a hard mask can be further enhanced.
Specific examples of the crosslinking agent include etherified amino resins, such as methylated or butylated melamine (specific examples include N-methoxymethyl-melamine or N-butoxymethyl-melamine) and methylated or butylated urea (urea) resin (specific examples include Cymel U-65 resin or UFR 80 resin), glycoluril derivatives represented by the following chemical formula 41 (specific examples include Powderlink 1174), bis (hydroxymethyl) -p-cresol compounds represented by the chemical formula 42), and the like. Further, a bicyclo oxygen compound represented by the following chemical formula 43 and a melamine compound represented by the following chemical formula 44 may be used as the crosslinking agent.
[ chemical formula 41]
Figure BDA0001263713510000141
[ chemical formula 42]
Figure BDA0001263713510000142
[ chemical formula 43]
Figure BDA0001263713510000143
[ chemical formula 44]
Figure BDA0001263713510000144
As the catalyst, an acid catalyst or a basic catalyst can be used.
The acid catalyst may be a thermally activated acid catalyst. As an example of the acid catalyst, an organic acid such as p-toluenesulfonic acid monohydrate (p-toluene sulfonic acid monohydrate) can be used, and a tag (thermal acid generator) type compound having storage stability can be mentioned. The thermal acid generator is an acid generator compound which releases an acid upon heat treatment, and for example, pyridine p-toluenesulfonate can be used
Figure BDA0001263713510000145
Salts (pyridine p-toluene sulfonate), 2,4,4, 6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, alkyl esters of organic sulfonic acids, and the like.
As the above-mentioned basic catalyst, NH may be used4OH or selected from NR4And (d) any one of ammonium hydroxides represented by OH (R is an alkyl group).
In addition, other photosensitive catalysts known in the art of resist technology may be used as long as they are compatible with the other components of the antireflective composition.
When the crosslinking agent is contained, the content of the crosslinking agent may be 1 to 30 parts by weight, preferably 5 to 20 parts by weight, and more preferably 5 to 10 parts by weight, based on 100 parts by weight of the compound (a). When the catalyst is contained, the content of the catalyst may be 0.001 to 5 parts by weight, preferably 0.1 to 2 parts by weight, and more preferably 0.1 to 1 part by weight, based on 100 parts by weight of the compound (a).
When the content of the crosslinking agent is in the above range, appropriate crosslinking characteristics can be obtained while maintaining optical characteristics of the formed underlayer film.
When the catalyst content is within the above range, the acidity that affects the storage stability can be appropriately maintained while appropriate crosslinking characteristics are obtained.
Additive agent
The composition for a hard mask of the present invention may further contain an additive such as a surfactant, if necessary. As the surfactant, alkyl benzene sulfonate and alkyl pyridine can be used
Figure BDA0001263713510000151
Salts, polyethylene glycols, quaternary ammonium salts, and the like, but are not limited thereto. In this case, the content of the surfactant may be 0.1 to 10 parts by weight based on 100 parts by weight of the compound (a). When the content of the surfactant is within the above range, appropriate crosslinking characteristics can be obtained while maintaining the optical characteristics of the formed underlayer film.
Hereinafter, preferred embodiments are provided to help understanding of the present invention, but these embodiments are merely illustrative of the present invention and do not limit the scope of the appended claims, and various changes and modifications of the embodiments within the scope and technical spirit of the present invention, which will be apparent to those skilled in the art, are of course also included in the scope of the appended claims.
Examples and comparative examples
Compositions for hard masks having the compositions and contents (wt%) shown in tables 1 and 2 below were prepared.
[ Table 1]
Figure BDA0001263713510000161
[ Table 2]
Figure BDA0001263713510000162
A-1:
Figure BDA0001263713510000163
A-2:
Figure BDA0001263713510000171
A-3:
Figure BDA0001263713510000172
A-4:
Figure BDA0001263713510000173
A-5:
Figure BDA0001263713510000174
A’-1:
Figure BDA0001263713510000175
A’-2:
Figure BDA0001263713510000176
A’-3:
Figure BDA0001263713510000181
B-1: propylene Glycol Monomethyl Ether Acetate (PGMEA)
C-1: n-methoxymethyl-melamine
D-1: pyridine p-toluenesulfonate
Figure BDA0001263713510000182
Salt (salt)
E-1: triethylene glycol
Examples of the experiments
1. Evaluation of Heat resistance
The composition was vacuum dried to remove the solvent, a portion of the sample was taken, and the mass loss rate was measured by thermogravimetric analysis (TGA) under nitrogen while the temperature was raised to 800 ℃.
Mass loss rate { (initial mass-800 ℃ mass)/initial mass } x 100%
< determination of Heat resistance >
Very good: the mass loss rate is less than 10 percent
O: the mass loss rate is more than 10 percent and less than 15 percent
And (delta): the mass loss rate is more than 15 percent and less than 25 percent
X: the mass loss rate is more than 25 percent
2. Etch selectivity
The sample solutions prepared in examples 1 to 14 and comparative examples 1 to 5 were respectively coated on a silicon wafer by a spin coating method, and baked at 200 ℃ for 60 seconds to a thickness
Figure BDA0001263713510000183
The film of (1). The resulting films were coated with a photoresist for ArF, baked at 110 ℃ for 60 seconds, exposed to light using an exposure apparatus from ASML (XT:1450G, NA 0.93.93), and developed with TMAH (2.38 wt% aqueous solution) to obtain a line and space (line and space) pattern of 60 nm.
The resulting patterned test piece was further cured at 110 ℃ for 60 seconds using CHF3/CF4The test pieces were dry-etched with the mixed gas for 20 seconds, and the etching rates were measured by observing the cross sections through the FE-SEM, thereby determining the etching resistance to halogen plasma, i.e., the etching selectivity.
< determination of etching resistance to halogen gas >
Very good: the etching speed is less than 10A/Sec
O: an etching rate of 10A/Sec or more and less than 11A/Sec
And (delta): an etching rate of 11A/Sec or more and less than 12A/Sec
X: the etching rate is more than 12A/Sec
[ Table 3]
Figure BDA0001263713510000191
Referring to table 3, it was confirmed that the examples exhibited excellent heat resistance and etching selectivity, and the comparative examples exhibited poor heat resistance and etching selectivity.

Claims (7)

1. A hardmask composition comprising a compound having two or more tertiary alcohol groups in a molecule and a solvent,
the compound is at least one selected from the group consisting of compounds represented by the following chemical formulas 1 to 3:
chemical formula 1
Figure FDA0003261106530000011
Wherein n is 1 to 10,
R1and R2Each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Ar1each independently an arylene group having 6 to 20 carbon atoms,
Ar2and Ar3Each independently an aryl group having 6 to 20 carbon atoms,
ar is1、Ar2、Ar3、R1And R2Can be independently substituted by-OH, -ORa、-OAra、-Ra、-AraFurther substituted, said-RaIs aliphatic hydrocarbon group with 1-6 carbon atoms, and the-AraAn aryl group having 6 to 20 carbon atoms,
chemical formula 2
Figure FDA0003261106530000012
Wherein n is 2 to 10,
R3each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Ar4an aryl group having 6 to 20 carbon atoms wherein n hydrogen atoms may be substituted,
Ar5each independently an aryl group having 6 to 20 carbon atoms,
the R is3、Ar4And Ar5Can be independently substituted by-OH, -ORa、-OAra、-Ra、-AraFurther substituted, said-RaIs aliphatic hydrocarbon group with 1-6 carbon atoms, and the-AraAn aryl group having 6 to 20 carbon atoms,
chemical formula 3
Figure FDA0003261106530000021
In the formula, R4And R5Each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,
Ar6and Ar7Each independently an arylene group having 6 to 20 carbon atoms,
the R is4、R5、Ar6And Ar7Can be independently substituted by-OH, -ORa、-OAra、-Ra、-AraFurther substituted, said-RaIs aliphatic hydrocarbon group with 1-6 carbon atoms, and the-AraIs an aryl group having 6 to 20 carbon atoms.
2. The hardmask composition according to claim 1, the Ar1、Ar6And Ar7Each independently is phenylene, naphthalene diyl, anthracene diyl, stilbene diyl, or pyrenediyl.
3. The hardmask composition according to claim 1, the Ar2、Ar3And Ar5Each independently is phenyl, naphthyl, anthryl, stilbenyl or pyrenyl.
4. The hardmask composition according to claim 1, the Ar4Is phenyl,Naphthyl, anthryl, stilbenyl or pyrenyl.
5. The hardmask composition according to claim 1, wherein R1~R5Each independently being methyl, vinyl, allyl or phenyl.
6. The hardmask composition according to claim 1, comprising 10 to 70 wt% of the compound and 30 to 90 wt% of the solvent, based on the total weight of the composition.
7. The hardmask composition according to claim 1, further comprising at least one of a crosslinker and a catalyst.
CN201710220902.XA 2016-04-29 2017-04-06 Composition for hard mask Active CN107340687B (en)

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KR1020160053110A KR102539857B1 (en) 2016-04-29 2016-04-29 Composition for hard mask

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