The degree of crosslinking, the thickness uniformity, the etching rate, the degree of fume generation, and the degree of crosslinking of the antireflection film, which were produced from the antireflection film compositions of Examples 5 to 8 and Comparative Example 1, The results of observing the pattern shape of the developed photoresist are shown in Table 2 below.

In contrast, in Table 2, in the case of Comparative Example 1 using poly (4-hydroxystyrene) having a low refractive index, the thickness of the antireflection film produced using the same was not uniform, the etching rate was slow, It can be confirmed that the pattern shape of the photoresist present on the top is not good. Particularly, as a result of observing the pattern shape of the photoresist, when the antireflection film was produced by using the antireflection film composition of Comparative Example 1, in the photoresist film existing on the antireflection film, a standing wave Wave pattern on the pattern wall part).

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However, the anti-reflection film acts as a stumbling block in the process of etching the metal film existing under the photoresist film having the pattern formed thereon in the semiconductor lithography process. Korean Patent Publication No. 10-1301464 discloses an antireflection film comprising an organic compound. US Patent No. US 6414146 discloses an isocyanurate compound useful as an organic antireflection film and a method of synthesizing the same. However, the organic compound according to the prior art has a low stability in a high temperature environment, has a low refractive index, is soluble in an organic solvent, and forms a thick antireflection film. In the process of coating a photoresist on the antireflection film, The organic compound contained in the organic solvent is dissolved in the organic solvent and mixed with the photoresist, thereby adversely affecting pattern formation. In addition, since the organic compound contains a high content of carbon, the anti-reflection film containing the compound has a slow etching rate compared to the photoresist film, so that the etching process is performed smoothly using the upper photoresist film as a mask And thus the photoresist film is largely lost.

In addition, the present invention provides a method of manufacturing a semiconductor device, comprising: (1) applying an antireflection film composition onto a wafer; And (2) heating the wafer coated with the anti-reflective coating composition; To a process for producing an antireflection film for a semiconductor process.

The present invention relates to a polyurethane compound having excellent coating properties and exhibiting a high refractive index and an excellent etching rate, comprising at least one polyisocyanate selected from compounds represented by the following general formulas (1) and (2) And a polyurethane compound produced through condensation polymerization of a polyhydric alcohol.

In Formula 1-1, Formula 2-2, Formula 1-2a, and Formula 1-2b, R may be any one selected from the group consisting of R 1 to R 3 , and A is A 1 to A 3 And R 1 to R 3 are the same as defined in Formula 1, and A 1 to A 3 are the same as defined in Formula 3. The definition of R < 4 > is the same as defined in Formula 2, of May be a bonding chain comprising a urethane group or hydrogen, of May be a bonding chain including a urethane group, and n, m, p, and q may be an integer of 1 to 1000.

The present invention also relates to an antireflection film composition for a semiconductor process comprising the polyurethane compound.

The present invention also relates to an antireflection film composition for a semiconductor process comprising the polyurethane compound.

The antireflection film compositions prepared in Examples 5 to 8 and Comparative Example 1 were spin-coated on a wafer and heated (baked) at 230 DEG C for 60 seconds. Thereafter, the degree of fume generation and the thickness of the coating film were measured with an ellipsometer Were measured using an Elipsometer (FE-5000, Otsukael, Japan). The photoresist was coated on the antireflection film, and then exposed and developed at 193 nm. The pattern shape was observed using a scanning electron microscope (SEM).

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An anti-reflective coating composition was prepared according to the composition shown in Table 1 below. As the resin, one of the polyurethane compounds A to D was selected and used. As the crosslinking agent, 1,3,4,6-tetrakis (methoxymethyl) glycoluril of the formula (3) was used. As the acid generator, pyridinium p- And toluidine sulfonate (pyridinium p-toluenesulfonate) was used. Propylene glycol monomethyl acetate (PGMEA) was used as a solvent. The polyurethane compound (resin), the crosslinking agent and the acid catalyst were dissolved in 100 g of the solvent according to the contents of Table 1, and then the particulate impurities were completely removed using a 0.05 mu m filter.

A 1 to A 2 independently represent a substituted or unsubstituted (C 1 -C 20) alkylene group, a substituted or unsubstituted (C 2 -C 20) alkenylene group, a substituted or unsubstituted (C 6 -C 30) Or an unsubstituted (C3-C30) heteroarylene group, and the like;

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Hereinafter, the present invention will be described in more detail with reference to the following examples. However, these examples are only for the understanding of the present invention, and the scope of the present invention is not limited by the following examples.

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In a flask, 20 g of hexamethylene diisocyanate trimer and 23 g of bis (2-hydroxyethyl) methyl isocyanurate were dissolved in 200 g of dimethylformamide, and then 10 g of triethylamine And the reaction temperature was raised to 80 ° C. After stirring at this temperature for 5 hours, the polymerized polyurethane compound was precipitated by dripping into deionized water with high excess of neutralization. The precipitated compound was filtered and dried to obtain 33 g of a polyurethane compound D. The weight average molecular weight of the compound D in terms of polystyrene was 5,800.

In the semiconductor manufacturing process, the antireflection film has three functions. First, it has the function of absorbing the laser light reflected from the wafer substrate. This is to optimize the pattern shape by minimizing the reflection of laser light used during the exposure process. However, when the refractive index is low, the thickness of the antireflection film increases, which is a disadvantage in the etching process. It can be said that a compound having a high refractive index is more suitable as an antireflection film material for this purpose.

Secondly, the function of improving the adhesion of photoresist to the surface of the wafer, the general organic compound has a low adhesion with the wafer. When the photoresist is applied to the surface of the wafer without using the antireflection film and then patterned, many phenomena that the pattern is separated from the wafer surface occur. However, when the patterning process of the photoresist is performed after the application of the antireflection film, the phenomenon that the pattern is separated from the wafer surface is remarkably reduced.

R 1 to R 4 independently represent a substituted or unsubstituted (C 1 -C 20) alkylene group, a substituted or unsubstituted (C 1 -C 20) cycloalkylene group, a substituted or unsubstituted (C 2 -C 20) alkenylene group, A substituted or unsubstituted (C6-C30) arylene group, and a substituted or unsubstituted (C3-C30) heteroarylene group;

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20 g of hexamethylene diisocyanate trimer and 31 g of tris (2-hydroxyethyl) isocyanurate were dissolved in 250 g of dimethylformamide, and 15 g of triethylamine was added to the flask. And the reaction temperature was raised to 80 ° C. The mixture was stirred at this temperature for 5 hours, neutralized and added dropwise to deionized water to precipitate the polymerized polyurethane compound. The precipitated compound was filtered and dried to obtain 35 g of polyurethane compound A. The polystyrene reduced weight average molecular weight of Compound A was 8,100.

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R 1 to R 4 independently represent a substituted or unsubstituted (C 1 -C 20) alkylene group, a substituted or unsubstituted (C 1 -C 20) cycloalkylene group, a substituted or unsubstituted (C 2 -C 20) alkenylene group, A substituted or unsubstituted (C6-C30) arylene group and a substituted or unsubstituted (C3-C30) heteroarylene group;

The antireflection film composition of the present invention may contain 0.1 to 10% by weight, preferably 0.5 to 3% by weight of the polyurethane compound based on the total weight of the total antireflection film composition. The content of the polyurethane compound in the antireflection film composition is not particularly limited, but it is preferable to satisfy the above content range because a high refractive index and an excellent etching rate can be exhibited.

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A 3 is any one selected from the group consisting of hydrogen, (C 1 -C 20) alkyl group, (C 1 -C 20) alkenyl group, (C 6 -C 30) aryl group, (C 3 -C 30) heteroaryl group, . ≪ / RTI >

The present invention also provides a method for manufacturing a semiconductor device, comprising the steps of: (1) applying an antireflection film composition selected from the above items 2 to 7 onto a wafer; And (2) heating the wafer coated with the anti-reflective coating composition; And a method of manufacturing an antireflection film for a semiconductor process.

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As the reaction catalyst used in the condensation polymerization reaction, at least one basic compound selected from the group consisting of a tertiary amine compound, a pyridine derivative, an imidazole derivative, and a strong base may be used. Specific examples thereof include triethylamine, One or more compounds selected from the group consisting of ethylamine, propylamine, pyridine, dimethylaminopyridine, 1,8-Diazabicycloundec-7-ene and TEDA (triethylene diamine) may be used, It does not. The solvent used in the condensation polymerization reaction is not particularly limited as long as it is an organic solvent, but it is preferable to dissolve the polyvalent isocyanate and the polyhydric alcohol monomer, and it is possible to dissolve the polyvalent isocyanate and the polyvalent alcohol monomer, have. Examples of the compound that can be used as the solvent include acetone, methyl ethyl ketone, methylene chloride, chloroform, acetonitrile, dimethylformamide, dimethylacetamide, methylpyrrolidone, tetrahydrofuran and ethyl acetate. Preferably, acetonitrile, dimethylformamide, dimethylacetamide, methylpyrrolidone, and tetrahydrofuran can be used as the solvent, but are not limited thereto. In the synthesis of the polyurethane compound of the present invention, the condensation polymerization reaction may be carried out at a temperature of 25 to 200 캜, such as a conventional condensation polymerization reaction, preferably 30 to 150 캜, more preferably 50 And the reaction temperature may be varied depending on the catalyst and the solvent used in the condensation polymerization reaction. As described above, in the present invention, the temperature condition of the condensation polymerization reaction is not particularly limited. However, when the above range is satisfied, the polymerization reaction time can be shortened and the amount of impurities produced during the condensation polymerization reaction can be minimized Most preferred.

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Thirdly, it is a function to planarize the wafer surface with the step difference. When the wafer surface has a step, the accuracy of pattern formation in the exposure step is very low. This is because the lens focus (Focus) is not matched in the exposure process and the pattern accuracy is lowered. In order to minimize the level difference of the wafer surface, a low-molecular compound is advantageous rather than a polymer compound. In the case of the polymer compound, the mass transfer during the curing process after coating is small, while in the case of the low molecular compound, the mass transfer during the curing process actively progresses and the planarization proceeds accordingly.

The novel polyurethane polymer according to the present invention is a core material contained in an antireflection film composition for a semiconductor manufacturing process, and has a high refractive index, a high etching rate, and excellent coating properties. Since the antireflection film composition of the present invention contains the above-mentioned polyurethane polymer compound, it is possible to manufacture a thin antireflection film having a small thickness, and it has no solubility in an organic solvent, thereby minimizing the possibility of pattern defect in the photoresist.

In the specification, " substituted " means that in the structure constituting the compound or the compound, the hydrogen element bonded to the carbon element is a nitro group, a C1-C7 alkyl group, a C1-C10 cycloalkyl group, a C1-C7 alkoxy group, An aryl group, a C3-C30 heteroaryl group, and the like.

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Hereinafter, the polyurethane compound and the antireflection film composition containing the same according to the present invention will be described in detail. The following embodiments are provided by way of example so that those skilled in the art can fully understand the spirit of the present invention. It will be apparent to those skilled in the art that, unless otherwise defined, technical terms and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs, And a description of the known function and configuration will be omitted.

The organic solvent that may be included in the antireflection film composition of the present invention is at least one selected from the group consisting of cyclohexanone, 2-heptanone, propylene glycol monomethyl ether, propylene glycol monomethyl acetate, gamma-butyrolactone, ethyl lactate, dimethylsulfoxide, dimethyl Acetamide, and N-methylpyrrolidone, but the present invention is not limited thereto.

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Except that poly (4-hydroxystyrene) (Sigma Aldrich, USA) (hereinafter referred to as Compound E) having a polystyrene equivalent weight average molecular weight of 6,500 was used as a resin in Example 5 The antireflection film composition was prepared by the same composition and method.

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In the antireflection film composition of the present invention, the crosslinking agent is for crosslinking the polyurethane compound containing a part of the unreacted functional group to form an antireflection film, and includes triglycidyl isocyanurate and a compound represented by the following general formula Or a compound thereof. In the present invention, the crosslinking agent may be included in an amount of 0.5 to 35 parts by weight, preferably 2 to 20 parts by weight, based on 100 parts by weight of the polyurethane compound.

In the method for producing an antireflection film of the present invention, heating in the step (2) is carried out by maintaining the temperature at 150 to 300 ° C, preferably 200 to 250 ° C for 15 to 300 seconds, preferably 45 to 180 seconds . The temperature and time range for heating the wafer coated with the antireflection film composition are not particularly limited. However, when the above range is satisfied, the antireflection film composition is not burned by heat and the crosslinking reaction can be completely performed. Antireflection film can be efficiently produced.

The present invention has been made to solve the above-mentioned problems, and provides a polyurethane compound having no solubility in an organic solvent, a high refractive index, and a high etching rate, and the polyurethane compound, including the polyurethane compound, It is an object of the present invention to provide an antireflection film composition capable of minimizing the occurrence of pattern defects.

The present invention relates to an antireflection film composition for use in a semiconductor lithography process, and more particularly, to a novel antireflection film composition for minimizing the possibility of pattern defect in photoresist by minimizing light reflected from a substrate during a semiconductor lithography process. And an antireflection film composition containing the same.

The thickness of the photoresist film is continuously decreasing in order to miniaturize the pattern. The higher the thickness, the lower the resolution of the pattern, and the lower the stability of the formed pattern, causing the pattern to collapse or warp. In order to form a good pattern using a photoresist, the use of an antireflection film is essential. The antireflection film is a functional film coated on a substrate and positioned directly below the photoresist film. This is because the use of the antireflection film can improve the adhesion of the pattern and optimize the pattern shape by minimizing the laser reflection. If the antireflection film is not used, not only the adhesion force is lowered but also the pattern is deformed by the light reflected from the substrate.

The polyurethane compound of the present invention can be specifically represented by the following formulas (1-1), (2-2), (1-2a) and (1-2b), but is not particularly limited thereto.

A 3 is any one selected from the group consisting of hydrogen, (C 1 -C 20) alkyl group, (C 1 -C 20) alkenyl group, (C 6 -C 30) aryl group, (C 3 -C 30) heteroaryl group and (C 1 -C 20) . ≪ / RTI >

The polyurethane compound of the present invention produced by the above condensation polymerization may have a wide variety of molecular weights, and by using an excess of one of the polyvalent isocyanates and polyhydric alcohols of the present invention used in the condensation polymerization reaction, The average molecular weight of the compound can be controlled.

20 g of hexamethylene diisocyanate and 38 g of bis (2-hydroxyethyl) methyl isocyanurate were dissolved in 300 g of dimethylformamide, and 20 g of triethylamine was added to the flask. And the reaction temperature was raised to 80 ° C. The mixture was stirred at this temperature for 5 hours, neutralized and added dropwise to deionized water to precipitate the polymerized polyurethane compound. The precipitated compound was filtered and dried to obtain 41 g of polyurethane compound B. The polystyrene reduced weight average molecular weight of Compound B was 6,500.

B 1 to B 4 independently of one another are a (C1-C10) alkyl group or a (C2-C10) alkenyl group; B 5 to B 10 independently represent a (C 1 -C 10) alkylene group or a (C 2 -C 10) alkenylene group;

Reflective compoundsfor metal

To the flask, 20 g of hexamethylene diisocyanate and 53 g of tris (2-hydroxyethyl) isocyanurate were dissolved in 350 g of dimethylformamide, 25 g of triethylamine was added, The temperature was raised to 80 占 폚. The mixture was stirred at this temperature for 5 hours, neutralized and added dropwise to deionized water to precipitate the polymerized polyurethane compound. The precipitated compound was filtered and dried to obtain 48 g of polyurethane compound C. The polystyrene reduced weight average molecular weight of the compound C was 4,200.

The polyurethane compound of the present invention may have an average molecular weight in terms of a styrene equivalent of 500 to 30,000, and the average molecular weight of the polyurethane compound may be controlled by excessively using the polyhydric alcohol of the formula (3) . The average molecular weight of the polyurethane compound in terms of styrene is not particularly limited. When the polyurethane compound is in the above range, the polyurethane compound has excellent solubility in an organic solvent and coating properties, and as an antireflection film composition for semiconductor processing And can be suitably used. Also, the compound used in an excessive amount in the condensation polymerization reaction is not particularly limited. However, in the case of the polyurethane compound prepared by using the polyhydric alcohol in an excessive amount, the content of the isocyanate structure in the polyurethane compound increases, When the content of carbon in the polyurethane compound is low and the content of oxygen and nitrogen atoms is increased and the compound is included in the antireflection film composition for semiconductor processing, It is preferable to use an excessive amount of a polyhydric alcohol of the formula (3) in the condensation polymerization reaction.

It can be seen from the results of Table 2 that the antireflection films prepared using the antireflection film compositions according to Examples 5 to 8 of the present invention have excellent thickness uniformity and high etching rate. In addition, when the antireflection film was produced using the antireflection film compositions of Examples 5 to 8, it was found that the antireflection film composition of the present invention was excellent in the pattern shape of the photoresist existing on the antireflection film, And the amount of fume generated is very small. Thus, the anti-reflective coating composition of the present invention can minimize the contamination of devices used in the production of the anti-reflection coating It can be understood that there is an effect that can be achieved.

In the present invention, the polyurethane compound contained in the antireflection film composition may have an average molecular weight in terms of styrene of 500 to 30,000, preferably 700 to 20,000. The average molecular weight of the polyurethane compound in terms of styrene is not particularly limited. When the polyurethane compound contained in the antireflection film composition of the present invention satisfies the average molecular weight in terms of the styrene content in the above range, the antireflection film composition has a refractive index An antireflection film having a thin, uniform, and fast etching rate capable of minimizing the possibility of occurrence of a pattern shape defect of a photoresist due to its high solubility, low carbon content, excellent solubility in an organic solvent, and excellent coating property It is possible to manufacture it.

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The present invention relates to a polyurethane compound produced by condensation polymerization of at least one polyisocyanate selected from the compounds represented by the following general formulas (1) and (2) and a polyhydric alcohol represented by the following general formula (3).

The polyurethane compound of the present invention can be produced by reacting at least one polyisocyanate selected from the compounds represented by the formulas (1) and (2) and a polyvalent isocyanate represented by the formula (3) Can be synthesized by condensation polymerization of alcohol.

In the antireflection film composition of the present invention, the surfactant is specifically a nonionic surfactant including polyoxyethylene alkylaryl ethers. The content of the surfactant is not particularly limited, but may be 0.01 To 0.05 part by weight.

More preferably, in the above Chemical Formulas 1 to 3, R 1 to R 4 independently represent a substituted or unsubstituted (C 1 -C 20) alkylene group, a substituted or unsubstituted (C 2 -C 20) alkenylene group and a substituted Or a substituted or unsubstituted (C1-C20) cycloalkylene group, wherein A 1 to A 2 independently represent a substituted or unsubstituted (C1-C20) alkylene group and a substituted or unsubstituted C2-C20) alkenylene group, but the present invention is not limited thereto.

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Further, throughout the specification, " alkyl group " includes both straight chain alkyl groups and branched alkyl groups, and includes primary alkyl groups, secondary alkyl groups and tertiary alkyl groups unless otherwise specified.

A 1 to A 2 independently represent a substituted or unsubstituted (C 1 -C 20) alkylene group, a substituted or unsubstituted (C 2 -C 20) alkenylene group, a substituted or unsubstituted (C 6 -C 30) Or an unsubstituted (C3-C30) heteroarylene group;

In the antireflection film composition of the present invention, the acid generator refers to a compound which generates an acid upon exposure to light. The antioxidant is used as a catalyst for activating a crosslinking and curing reaction occurring in the production of an antireflection film. To compounds represented by the general formula (10). In the present invention, the acid generator may be added in an amount of 0.05 to 10 parts by weight, preferably 0.5 to 5 parts by weight, based on 100 parts by weight of the polyurethane compound, but is not particularly limited thereto.

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The antireflection film composition of the present invention may further include at least one selected from a crosslinking agent, an acid generator (acid catalyst), an organic solvent, and a surfactant.

Recently, ultra-fine patterns of 0.10 micron or less have been required in the manufacture of super LSI and the like due to the high integration of semiconductor devices. Accordingly, the exposure wavelength has become shorter in the conventional g line or i line area, Research on lithography using an excimer laser or an ArF excimer laser has attracted attention. In order to miniaturize semiconductor wirings, technology development in the photolithography process, which is a preceding process, must be preceded. In particular, the resolution of a photoresist in a photolithography process is a factor that directly affects the miniaturization of semiconductor wirings. This is because miniaturization of the wiring is impossible unless the photoresist pattern is miniaturized.