KR101572594B1 - A Composition of Anti-Reflective Hardmask - Google Patents
A Composition of Anti-Reflective Hardmask Download PDFInfo
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- KR101572594B1 KR101572594B1 KR1020150046115A KR20150046115A KR101572594B1 KR 101572594 B1 KR101572594 B1 KR 101572594B1 KR 1020150046115 A KR1020150046115 A KR 1020150046115A KR 20150046115 A KR20150046115 A KR 20150046115A KR 101572594 B1 KR101572594 B1 KR 101572594B1
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
Abstract
Description
The present invention relates to a hard mask composition having antireflection film properties useful in a lithographic process, and is characterized by containing a carbazole-based aromatic ring having strong absorption in the ultraviolet wavelength range, and a polymer comprising the same ≪ / RTI >
In recent years, the semiconductor industry is becoming increasingly refined, and an effective lithographic process is essential to realize such ultra-fine technology. In particular, there is a growing demand for new materials for the hard mask process, which is essential for the etching process.
Generally, the hard mask film acts as an interlayer to transfer the fine pattern of the photoresist to the lower substrate layer through the selective etching process. Therefore, the hard mask layer is required to have properties such as chemical resistance, heat resistance and etching resistance so as to withstand the multiple etching process. Conventional hard mask membranes used amorphous carbon layer (ACL) membranes made by chemical vapor deposition (CVD). The disadvantages of these membranes are the high cost of facility investment, particles generated during processing, and opaque film quality. Due to the problem of photo align due to the many inconveniences.
Recently, a spin-on hardmask, which is formed by a spin-on coating method, has been introduced instead of this chemical vapor deposition method. In the spin-on coating method, a hard mask composition is formed using an organic polymer material having solubility in a solvent. In this case, the most important characteristic is that an organic polymer coating film having etching resistance at the same time must be formed.
However, two properties required for such an organic hard mask layer, that is, solubility and etching resistance, are in conflict with each other, and a hard mask composition capable of satisfying all of them is required. The materials introduced into the semiconductor lithography process while satisfying the characteristics of the organic hard mask material have recently been introduced (Patent Publication 10-2009-0120827, Patent Publication 10-2008-0107210, Patent WO 2013100365 A1) And hard mask materials using a copolymer having an appropriate polymer molecular weight using hydroxypyrene.
On the other hand, recently, as the semiconductor lithography process is further miniaturized, in the case of such an organic hard mask material, it is difficult to sufficiently fulfill the role as a mask due to the lack of the etching selection ratio in the etching process compared with the existing inorganic hard mask material It was. Therefore, the introduction of an organic hard mask material more optimized for the etching process is desperately needed.
The present invention relates to a novel organic hard mask material having sufficient etching resistance and high solubility in such organic hard mask materials.
SUMMARY OF THE INVENTION The present invention has been made to solve the problems of the prior art as described above and it is an object of the present invention to provide an antireflective composition which is high in etching selectivity, resistant to multiple etching, It is an object of the present invention to provide a novel hard mask polymer which can be used to perform graphic techniques and a composition comprising the same.
According to the present invention,
A carbazole derivative polymer represented by the following formula (1) or a polymer blend comprising the same; And (b) an organic solvent.
[Chemical Formula 1]
In the above formula, R is an alkyl group in the form of hydrogen (H) or methyl, ethyl, ethyl alcohol, C3-C20 alkyl or aromatic ring, and has the following form.
On the other hand, X is bonded by a co-monomer component capable of conducting a one-to-one polymerization with an aromatic ring compound mainly under acid catalyzed condition, and the solubility of the formed polymer substance in a solvent is increased Linkage group, which has the following structure independently of each other. Is a compound having an aldehyde form such as paraformaldehyde, benzaldehyde or the like or a compound having a di-methoxy or di-ethoxy group and reacting with the carbazole derivative under an acid catalyst. An example of X is as follows.
And Y is a different type of aromatic compound having a hydroxyl group (OH), and is mainly introduced to improve the thermosetting reactivity and etch selectivity of the entire polymer structure, and each of them may have the following form.
(1 + m + n) = 0.05 to 0.45, m / (l + m = n) = 0.5 and n / The mass average molecular weight (Mw) of the coalescent is between 1,000 and 30,000. The not-mentioned hydroxyarylene refers to the formation of a conventional hydroxyarylene structure.
On the other hand, in order to make the hard mask composition, the carbazole-based aromatic ring-containing polymer (a) is preferably used in an amount of 1 to 30% by weight based on 100 parts by weight of the organic solvent (b) used. When the aromatic ring-containing polymer is used in an amount of less than 1 part by weight or more than 30 parts by weight, it is difficult to meet or exceed the desired coating thickness because the coating thickness is less than or exceeds the desired coating thickness.
The organic solvent is not particularly limited as long as it is an organic solvent having sufficient solubility in the above aromatic ring-containing polymer. Examples thereof include propylene glycol monomethyl ether acetate (PGMEA), cyclohexanone, ethyl lactate, and the like have.
The antireflective hard mask composition of the present invention may further comprise (c) a crosslinker component; And (d) an acid catalyst.
The crosslinking agent (c) used in the hard mask composition of the present invention is preferably capable of crosslinking the repeating units of the polymer by heating in a reaction catalyzed by the generated acid, and the acid catalyst (d) It is preferably an activated acid catalyst.
The crosslinking agent component (c) used in the hard mask composition of the present invention is not particularly limited as long as it is a crosslinking agent capable of reacting with the hydroxyl group of the aromatic ring-containing polymer in such a manner as to be catalyzed by the produced acid. Specific examples thereof include etherified amino resins such as methylated or butylated melamine resins (specific examples are N-methoxymethyl-melamine resins or N-butoxymethyl-melamine resins) and methylated Urea Resin (specific examples are Cymel U-65 Resin or UFR 80 Resin), glycoluril compounds (specific examples are Powderlink 1174), or bisepoxy compounds (specific examples include 2 , 6-bis (hydroxymethyl) -p-cresol compound), and the like.
As the acid catalyst (d) used in the hard mask composition of the present invention, an organic acid such as p-toluenesulfonic acid monohydrate may be used, and a thermal acid generator (TAG) Based compounds may also be used as catalysts. TAG is an acid generator compound which is intended to release an acid upon thermal treatment, such as pyridinium P-toluene sulfonate, 2,4,4,6-tetrabromocyclohexadienone, Benzoin tosylate, 2-nitrobenzyl tosylate, and alkyl esters of organic sulfonic acids.
Therefore, when the final hard mask composition further comprises (c) a crosslinking agent component and (d) an acid catalyst, the hard mask composition of the present invention comprises (a) a carbazole derivative having strong absorption properties in the ultraviolet region (C) 0.1 to 5% by weight, more preferably 0.1 to 3% by weight, of a cross-linking agent component is used in an amount of 1 to 30% by weight, more preferably 3 to 15% (D) 0.001 to 0.05 wt.%, More preferably 0.001 to 0.03 wt.% Of an acid catalyst, and (b) 100 wt.% Of an organic solvent as a balance component. By weight and 75 to 98% by weight.
Here, when the aromatic ring-containing polymer is less than 1% by weight or exceeds 30% by weight, it is difficult to meet or exceed the intended coating thickness because it is less than or exceeds the target coating thickness.
If the content of the crosslinking agent is less than 0.1% by weight, the crosslinking property may not be exhibited. If the amount is more than 5% by weight, the optical characteristics of the coating film may be changed by excessive addition.
If the amount of the acid catalyst is less than 0.001 wt%, crosslinking properties may not be exhibited. If the amount is more than 0.05 wt%, the acidity may increase due to excessive addition, which may affect storage stability.
The antireflective hard mask composition according to the present invention has a refractive index and absorptivity in a range that is useful as an antireflective film in a Deep UV region such as ArF (193 nm) and KrF (248 nm) at the time of film formation, thereby minimizing the reflectivity between the resist and the backside layer And it is possible to provide a lithographic structure having a good pattern evaluation result because it has a high etch selectivity in a lithographic process compared to a conventional organic hard mask and has sufficient resistance against multiple etching.
Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.
Production Example 1) Synthesis of carbazole-based cyclic polymer
- A 250 mL round flask was charged with 24.3 g (100 mmol) of 9-phenylcarbazole, 6.4 g (200 mmol) of paraformaldehyde and 14.4 g (100 mmol) of 1-naphthol with propylene glycol Dissolved in 107 g of monomethyl ether acetate (PGMEA), and 0.8 g of a sulfuric acid stock solution was added thereto.
- While maintaining the reaction temperature at about 120 ° C, the polymerization is proceeded while the molecular weight is measured using GPC in the middle of the reaction.
- After about 12 hours of reaction, the reaction mixture is dropped into an excess of methanol / water (9: 1) co-solvent, and the resulting solid is dissolved again in an appropriate amount of PGMEA solvent. Excess ethanol / water : 1) Drop in a co-solvent to catch a precipitate.
The resultant solid was dried in a vacuum oven at about 50 ° C for about 20 hours, and a 2,600 weight average molecular weight (Mw) polymer was obtained.
Production Example 2) Synthesis of carbazole-based cyclic polymer
(60mmol) of 9-phenylcarbazole, 20g (120mmol) of 1,4-bis (methoxymethyl) benzene (MBB) and 8.7g (60mmol) of 2-naphthol were dissolved in propylene glycol monomethyl ether acetate (PGMEA), and 0.5 g of a stock solution of sulfuric acid is added thereto.
- Polymerization was carried out in the same manner as in Production Example 1, and the polymer was purified and dried in a vacuum oven to obtain 2,800 polymer having a weight average molecular weight of 2,000.
Production Example 3) Synthesis of carbazole ring polymer
(60 mmol) of 9-naphthyl carbazole, 13 g (120 mmol) of benzaldehyde and 8.7 g (60 mmol) of 1-naphthol were dissolved in propylene glycol monomethyl ether acetate (PGMEA ), And then 0.5 g of a stock solution of sulfuric acid was added thereto.
- Polymerization was carried out in the same manner as in Production Example 1, and the polymer was purified and dried in a vacuum oven to obtain 2,700 weight average molecular weight polymer.
Production Example 4) Synthesis of carbazole ring polymer
(40 mmol) of 9- (9-phenanthryl) carbazole, 11 g (100 mmol) of benzaldehyde and 8.7 g (60 mmol) of 1-naphthol were dissolved in propylene glycol monomethyl ether acetate ), And 0.4 g of a stock solution of sulfuric acid was added thereto.
- Polymerization was carried out in the same manner as in Production Example 1, and the polymer was purified and dried in a vacuum oven to obtain a polymer having a weight average molecular weight of 3,000.
Production Example 5) Carbazole-based cyclic polymer synthesis
(60 mmol) of 9- (1-naphthyl) carbazole, 13 g (120 mmol) of benzaldehyde and 13 g (60 mmol) of 1-pyrenol were added to propylene glycol mono After dissolving in 93 g of methyl ether acetate (PGMEA), 0.5 g of a stock solution of sulfuric acid was added thereto.
- Polymerization was carried out in the same manner as in Preparation Example 1, and the polymer was purified and dried in a vacuum oven to obtain 2,900 weight average molecular weight polymer.
Production Example 6) Carbazole-based cyclic polymer synthesis
(60 mmol) of 9- (4-biphenyl) carbazole and 13 g (120 mmol) of benzaldehyde and 13 g (60 mmol) of 1-pyrenol were added to propylene glycol mono After dissolving in 107 g of methyl ether acetate (PGMEA), 0.5 g of a stock solution of sulfuric acid was added thereto.
- Polymerization was carried out in the same manner as in Preparation Example 1, and the polymer was purified and dried in a vacuum oven to obtain a polymer having a weight average molecular weight of 3,100.
Production Example 7) Synthesis of carbazole ring polymer
23 g (60 mmol) of 9- (1-pyrenyl) carbazole and 4.3 g of paraformaldehyde and 13 g (60 mmol) of 1-pyrenol were dissolved in propylene glycol monomethyl ether acetate PGMEA), and then 0.5 g of a stock solution of sulfuric acid was added thereto.
- Polymerization was carried out in the same manner as in Production Example 1, and the polymer was purified and dried in a vacuum oven to obtain a polymer having a weight average molecular weight of 3,000.
Production Example 8) Synthesis of carbazole-based cyclic polymer
(50 mmol) of 9-pyrenecarbazole, 3.6 g of paraformaldehyde and 17.5 g (50 mmol) of 9,9-bis (4-hydroxyphenyl) After dissolving in 93 g of glycol monomethyl ether acetate, 0.4 g of a stock solution of sulfuric acid was added thereto.
- Polymerization was carried out in the same manner as in Preparation Example 1, and the polymer was purified and dried in a vacuum oven to obtain a polymer having a weight average molecular weight of 3,100.
Production Example 9) Synthesis of carbazole ring polymer
(60 mmol) of 9-pyrenecarbazole, 20 g (120 mmol) of 1,4-bis (methoxymethyl) benzene (MBB) and 13 g (60 mmol) of 1-pyrene were dissolved in 130 g of propylene glycol monomethyl ether acetate , And 0.5 g of a stock solution of sulfuric acid is added thereto.
- Polymerization was carried out in the same manner as in Production Example 1, and the polymer was purified and dried in a vacuum oven to obtain 2,800 polymer having a weight average molecular weight of 2,000.
Production Example 10) Synthesis of carbazole ring polymer
(60 mmol) of 9-naphthylcarbazole, 20 g (120 mmol) of 1,4-bismethoxymethylbenzene (MBB) and 13 g (60 mmol) of 1-pyrene were dissolved in 119 g of propylene glycol monomethyl ether acetate , 0.5 g of a stock solution of sulfuric acid was added thereto.
- Polymerization was carried out in the same manner as in Production Example 1, and the polymer was purified and dried in a vacuum oven to obtain 2,800 polymer having a weight average molecular weight of 2,000.
Production Example 11) Carbazole-based cyclic polymer synthesis
(60 mmol) of 9H-Carbazole-9-ethanol, 13 g (120 mmol) of benzaldehyde and 13 g (60 mmol) of 1-pyrene were dissolved in 91 g of propylene glycol monomethyl ether acetate and then 0.5 g of a stock solution of sulfuric acid do.
- Polymerization was carried out in the same manner as in Production Example 1, and the polymer was purified and dried in a vacuum oven to obtain 2,800 polymer having a weight average molecular weight of 2,000.
Comparative Production Example 1) Synthesis of hydroxy naphthalene polymer
35 g (100 mmol) of 9,9-bis (4-hydroxyphenyl) fluorine and 17 g (100 mmol) of bismethoxymethylbenzene (MBB) were dissolved in 121 g of PGMEA, and 0.07 g of PTSA was added thereto.
- Polymerization was carried out in the same manner as in Production Example 1, and the polymer was purified and dried in a vacuum oven to obtain 3,500 weight average molecular weight polymer.
[Examples 1 to 11 and Comparative Example 1]
Hard mask composition manufacturing
- Each of the polymers prepared in Preparation Examples 1 to 11 and Comparative Preparation Example 1 was weighed in an amount of 0.9 g each, and 0.1 g of a glycoluril compound crosslinking agent (Powderlink 1174) and 1 mg of pyridinium P-toluene sulfonate were dissolved in propylene glycol And dissolved in 9 g of monomethyl ether acetate (PGMEA), followed by filtration to prepare sample solutions of Preparation Examples 1 to 11 and Comparative Preparation Example 1, respectively.
Each of the sample solutions prepared in Production Examples 1 to 11 and Comparative Production Example 1 was spin-coated on a silicon wafer and baked at 240 DEG C for 60 seconds to form a film having a thickness of 3000 ANGSTROM.
The refractive index n and the extinction coefficient k of the formed films were respectively determined. The instrument used was an Ellipsometer (manufactured by J. A. Woollam), and the measurement results are shown in Table 1.
As a result of the evaluation, it was confirmed that there is a refractive index and an absorbency which can be used as an antireflection film at ArF (193 nm) and KrF (248 nm) wavelengths. Typically, the refractive index range of a material used as a semiconductor antireflection film is about 1.4 to 1.8, and an important value is an extinction coefficient, which is better when the absorption degree is larger.
Lithographic evaluation of antireflective hard mask compositions
The sample solutions prepared in Preparation Examples 3, 5, 7 and 9 and Comparative Preparation Example 1 were each spin-coated on an aluminum-coated silicon wafer and baked at 240 ° C. for 60 seconds to form a coating film having a thickness of 3000 Å.
- KrF photoresist was coated on each of the formed coating films, baked at 110 ° C for 60 seconds, exposed using ASML (XT: 1400, NA 0.93) exposure equipment, and then exposed to 2.38 wt% aqueous solution of tetramethyl ammonium hydroxide (TMAH) Respectively for 60 seconds. Then, a line and space pattern of 90 nm was examined by using V-SEM, respectively, and the results are shown in Table 2 below. The exposure margin (margin) and the depth of focus (DoF) margin according to the variation of the distance between the light source and the light source according to the variation of the exposure amount were examined and recorded in Table 2. As a result of pattern evaluation, good results were confirmed in terms of profile and margin. Generally, when the EL and DoF margin are 0.2 or more in the litho pattern evaluation, there is no problem in use.
(? MJ / energy mJ)
(탆)
Evaluation of etch characteristics for antireflective hard mask compositions
The lower SiON antireflection film (BARC) was dry-etched using the PRM as a mask with CHF 3 / CF 4 mixed gas in each of the patterns formed in Production Examples 5, 7 and 9 and Comparative Production Example 1, Using the SiON antireflection film as a mask, dry etching of the hard mask was performed again. After the dry etching of the silicon nitride (SiN) film with the CHF3 / CF4 mixed gas as a mask, O2 ashing and wet stripping processes were performed on the remaining hard mask and organic matter.
Immediately after hard mask etch and silicon nitride etch, the cross sections of each specimen were examined by V-SEM. As a result of the etch evaluation, after the hard mask etching and after the silicon nitride etching, the pattern shape was good without any bowing phenomenon in each case, so that the resistance against the etching process was sufficient and the etching process of the silicon nitride film was satisfactorily performed Respectively.
Claims (5)
(b) an organic solvent;
≪ / RTI >
[Chemical Formula 1]
(Wherein R is an alkyl group in the form of an aromatic ring selected from the following substituents,
X is any one selected from the following substituents,
Y is an aromatic ring compound having a hydroxy group (OH), and is any one selected from the following substituents.
(1 + m + n) = 0.05 to 0.45, m / (l + m = n) = 0.5 and n / The weight-average molecular weight (Mw) of the cohesive is between 1,000 and 30,000.
Wherein the hard mask composition further comprises a crosslinker and an acid catalyst component.
The hardmask composition may further comprise:
(a) 1 to 30% by weight of a polymer made from a carbazole derivative or a polymer blend comprising the same;
(b) 0.1 to 5% by weight of a crosslinker component;
(c) 0.001 to 0.05% by weight of an acid catalyst; And
(d) an organic solvent is used as the remaining component, and the total amount is 100% by weight.
Wherein the cross-linking component is any one selected from the group consisting of a melamine resin, an amino resin, a glycoluril compound, and a bis-epoxy compound.
The acid catalyst is selected from the group consisting of p-toluenesulfonic acid monohydrate, pyridinium p-toluene sulfonate, 2,4,4,6-tetrabromocyclohexadienone, benzo An alkylsulfonate, an alkylsulfonate, an alkylsulfonate, an alkylsulfonate, an alkylsulfonate, an alkylsulfonate, an alkylsulfonate, an alkylsulfonate, an alkylsulfonate, an alkylsulfonate,
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| KR101770749B1 (en) | 2016-01-11 | 2017-08-23 | 최상준 | A Composition of Anti-Reflective Hardmask |
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