KR100894403B1 - Co-polymer containing alkyl substituted ketoxime protected isocyante-based derivative, preparing method thereof, organic anti-reflective coating composition containing the co-polymer and organic anti-reflective coating using the composition - Google Patents

Abstract

The present invention is a copolymer containing an alkyl-substituted ketone oxime-protected isocyanate derivative, which can be used in ultrafine circuit processing process using far ultraviolet rays in the manufacture of semiconductor devices, a method for preparing the copolymer, an organic reflection containing the copolymer An anti-reflective composition, an organic anti-reflective coating using the composition, and a method for producing the same.

The organic anti-reflection film using a copolymer containing an alkyl-substituted ketone oxime-protected isocyanate derivative, when used in the manufacture of highly integrated devices of gigabit DRAM, improves the adhesion to the substrate and the interlayer reflection and standing wave phenomenon of the circuit By suppressing this, it is possible to stably form a high resolution microcircuit of 60 nm to 150 nm, thereby increasing the production yield of the semiconductor device.

Organic Anti-reflective Film, Isocyanate Cross-linked Copolymer Containing Alkyl-Cutred Ketone Oxime

Description

Copolymer containing an isocyanate derivative protected by alkyl-substituted ketooxime, a method for preparing the copolymer, an organic antireflective coating composition containing the copolymer and an organic antireflective coating using the composition {Co-polymer containing alkyl substituted ketoxime protected isocyante-based derivative, preparing method apparent, organic anti-reflective coating composition containing the co-polymer and organic anti-reflective coating using the composition}

The present invention, in photolithography, which is an exposure process for forming a microcircuit of a highly integrated semiconductor using short-wavelength ultraviolet light, suppresses reflective notching occurring in a substrate layer under a photoresist, Copolymer containing an alkyl-substituted ketone oxime-protected isocyanate derivative, which can remove the standing wave effect due to the change in thickness of the resist, a method for preparing the copolymer, an organic anti-reflective coating composition containing the copolymer It relates to an organic antireflection film using the composition and a method for producing the organic antireflection film.

An antireflective coating (ARC) is a very thin layer of light-absorbing photosensitive material, which is used to stably form ultrafine circuits of 60 nm to 150 nm and below, which are essential for producing gigabit (Gb) class ultra-high density semiconductors. Used in circuit processing process. Therefore, the anti-reflection film must be well matched with the high-resolution photoresist (PR) materials used in the existing semiconductor production process and mutual adhesion interface and optical properties.

Such an antireflection film is first applied to the bottom of the photoresist layer during the ultraviolet ray exposure process, and is called bottom antireflection film (BARC, bottom ARC), and an organic bottom antireflection film having high absorbance in the current highly integrated semiconductor optical microfabrication process. This is commonly used. Since the organic antireflection film must have high light absorption at a specific exposure wavelength, it must be able to cope with shortening of the light source (G-line, I-line, KrF, ArF, F2, etc.) according to the development of highly integrated semiconductor micromachining process. [M. Padmanaban et al., Proc. SPIE, 3678, 550 (1999); G. E. Bailey et al. Proc. SPIE, 3999, 521 (2000); M. Padmanaban et al., Proc. SPIE, 333, 206 (1998).

Recently, technology in the field of ultra high-density semiconductor fabrication has developed remarkably. However, only conventional optical microfabrication technology that rotates and exposes a photoresist, a photoresist, on a silicon wafer to expose a stable 60-150nm ultrafine circuit It has become impossible to do. Therefore, it is necessary to apply a special thin film to prevent reflection in the exposure process before applying the photoresist layer.

The anti-reflection film prevents standing wave effects caused by interference of incident light and reflected light from the substrate inside the photoresist layer during exposure, and also prevents reflection or corners due to topography resulting from a circuit layer made in a conventional process. It acts to prevent or significantly reduce diffuse reflection. Thus, precise control of the desired critical dimension ("CD") is achieved to increase the process latitude of the manufacturing process conditions. The anti-reflection film has an organic substance based on its composition and an inorganic substance using chemical vapor deposition. However, in recent years, most of the anti-reflective membranes which are convenient for the process are used.

The role of the anti-reflective film became more important after short-wavelength ultraviolet processing, especially after the process of optical microcircuit processing using a krypton fluoride (KrF) excimer laser having a wavelength of 248 nm, became more important. Organic polymer anti-reflective coating materials using chromophore-containing aromatic derivatives such as anthracene or naphthalene having high absorbance in the far ultraviolet region are widely used for circuit fabrication [J. Meador et al., Proc. SPIE, 3678, 800 (1999); G. Taylor et al., Proc. SPIE, 3678, 174 (1999); X. Shao et al., J. Photopolym. Sci. Techonol., 14, 481 (2001); Myoung Soo Kim et al., Proc. SPIE, 5753, 644 (2005); K. Mizutani et al., Proc. SPIE, 3678, 518 (1999). Such techniques are disclosed in US Pat. Nos. 5693691, 5886102, 5919599, 6033830, 6080530, 6156479 and 6602652.

Organic bottom anti-reflective coatings used in the ultra-violet exposure process for the fabrication of ultra-fine circuits must meet several requirements, such as [H. Yoshino et al., Proc. SPIE, 3333, 655 (1998); P. Trefonas et al., Proc. SPIE, 3678, 701 (1999); S. Malik et al., J. Photopolym. Sci. Techonol., 14, 489 (2001); R. Huang et al., Proc. SPIE, 5753, 637 (2005); C. Y. Chang et al., Proc. SPIE, 6153, 61530M (2006). The requirement must firstly have a refractive index n and a light absorption constant k, which are optical constants suitable for the light source used in semiconductor fabrication. Second, it should have a high selectivity at the plasma dry etching rate compared to the upper photoresist, and there should be no defects caused by dry etching. Third, intermixing should not occur between the photoresist layer and the anti-reflection film layer. For this purpose, a reactor capable of forming an appropriate crosslinked structure in the organic polymer chain should be included. Fourth, in the film forming process by rotational coating, suitable thin film thickness control ability, excellent coating film forming ability and coating film uniformity are required.

However, it is still insufficient to stably implement the organic bottom anti-reflection film that satisfies all the above conditions.

In order to solve the problems of the prior art, an object of the present invention is to expose a 248 nm wavelength krypton fluoride (KrF) and 193 nm wavelength argon fluoride (ArF) excimer laser Copolymer containing isocyanate derivatives protected with alkyl-substituted ketone oximes, which can be used in ultrafine circuit exposure processes, which can prevent diffuse reflection from lower layers during short wavelength exposure processes, and have excellent adhesion and crosslinking performance. It is to provide a manufacturing method.

Another object of the present invention is to provide an organic antireflection film composition containing the copolymer, an organic antireflection film using the composition, and a method of manufacturing the organic antireflection film.

The present invention is an organic antireflection film copolymer having a weight average molecular weight of 5,000 to 100,000 for a semiconductor microcircuit exposure process, characterized in that it contains an alkyl-substituted ketooxime protected isocyanate derivative represented by the following formula as a monomer. To provide.

<Formula 1>

In Formula 1, R and R ₁ are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkoxyalkyl group, a hydroxyalkyl group or a halogenated alkyl group, and R ₆ represents hydrogen or methyl.

The present invention is a weight average molecular weight, characterized in that the derivative represented by the formula (1) and the initiator is dissolved in a polymerization solvent and reacted according to the radical polymerization method for 2 to 24 hours at a temperature of 50 to 90 ℃ under an inert gas atmosphere Provided is a method for producing a copolymer of 5,000 to 100,000.

<Formula 2>

<Formula 3>

<Formula 4>

In Formulas 2 to 4, R ₂ represents an alkyl group having 1 to 6 carbon atoms, R ₃ is hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group, a hydroxyalkyl group or a halogenated alkyl group, and R ₄ and R ₅ are each independently Is hydrogen or methyl, x represents a natural number of 1 to 6, the mole fraction of the structural units represented by the formula 1 to 4 in the copolymer are k, l, m and n, respectively, based on the total mole fraction of the structural unit K is 0.1-0.7, l is 0-0.4, m is 0.1-0.7, n is 0.1-0.4.

The present invention is a copolymer; And it provides an organic antireflection film composition comprising an organic solvent.

The present invention provides an organic antireflection film comprising the organic antireflection film composition.

The organic anti-reflection film using a polymer having a copolymer as a basic structure according to the present invention has almost no gas generated even at high temperature thermal cross-linking due to covalent bonding of heat-crosslinkable isocyanate crosslinking groups into the polymer chain, thereby preventing safety from heat. outstanding. In addition, it has excellent adhesion with the substrate and has sufficient absorbance to have as an organic antireflection film, thereby suppressing reflections occurring in the lower layer during the exposure process and removing standing waves due to changes in thickness of the light source and photoresist used. In addition, the high etching ability to the plasma allows a stable transfer of the circuit to the substrate.

Therefore, when the copolymer according to the present invention is used as an organic anti-reflection film in an exposure process using an excimer laser having an exposure wavelength of 248 nm, 193 nm, or 157 nm in semiconductor manufacturing, a memory device of 1 gigabit DRAM or more or 60 nm to 150 nm The microcircuit fabrication of the system integrated circuit of the unit can be stably performed, thereby increasing the production yield of the semiconductor device.

 The organic antireflective coating composition according to the present invention has properties of monomers and copolymers containing anthracene chromophores that cause high light absorption at exposure wavelengths of 248 nm and 193 nm and alkyl-substituted ketooxime-protected isocyanate groups for crosslinking when antireflective films are formed. Binary copolymers, terpolymers or quaternary copolymers prepared from two or four different monomers, such as comonomers, for the purpose of control.

Hereinafter, the present invention will be described in detail.

One. Alkyl Substitution With ketone oxime  Copolymers Containing Protected Isocyanate-Based Derivatives

The copolymer of the present invention contains isocyanate derivatives protected with alkyl-substituted ketone oximes, more specifically methylethyl ketone oxime or ethylpropyl ketone oxime, contained as monomers, which are represented by the following formula (1). The derivative is a monomer that crosslinks by desorption of the protecting group by heat treatment during the exposure process in order to facilitate the preparation of the polymer used in the organic antireflection film.

<Formula 1>

In Formula 1, R and R ₁ are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkoxyalkyl group, a hydroxyalkyl group or a halogenated alkyl group, and R ₆ represents hydrogen or methyl.

Here, when said R and R <_1> is an alkyl group, an alkoxyalkyl group, a hydroxyalkyl group, or a halogenated alkyl group, when carbon number exceeds 10, there exists a problem of inferior crosslinkability.

In addition to the derivative of Formula 1, the copolymer of the present invention may contain one or two or more kinds selected from structural units represented by the following Formulas 2 to 4 as comonomers.

The structural unit represented by the following formula (2) is an alkylmaleimide monomer containing a hydroxy group, the structural unit represented by the following formula (3) is a (meth) acrylate monomer, and the structural unit represented by the following formula (4) is 9- Anthracene methyl methacrylate type monomer.

<Formula 2>

<Formula 3>

<Formula 4>

In Chemical Formulas 2 to 4,

R ₂ represents an alkyl group having 1 to 6 carbon atoms,

R ₃ is hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group, a hydroxyalkyl group or a halogenated alkyl group,

R ₄ and R ₅ are each independently hydrogen or methyl,

x represents the natural number of 1-6.

In the copolymer, the mole fractions of the structural units represented by Chemical Formulas 1 to 4 are k, l, m and n, respectively, based on the total mole fraction of the structural unit, k is 0.1 to 0.7, l is 0 to 0.4, and m is 0.1-0.7, n is 0.1-0.4.

When said R <_2> is an alkyl group, when carbon number exceeds 6, there exists a problem in heat resistance. When said R <_3> is an alkyl group, an alkoxyalkyl group, a hydroxyalkyl group, or a halogenated alkyl group, when carbon number exceeds 6, there exists a problem in optical property.

In addition, the copolymer may be represented by a copolymer represented by the following Structural Formula 1. In addition, each structural unit of the following structural formula 1 is not limited to the following structural formula 1 can be located at random.

<Structure 1>

The copolymer according to the present invention significantly improves the adhesion to the wafer compared to the conventional hydroxy-based crosslinked derivatives and exhibits an improved coating film formation ability by preventing intermixing with the photoresist layer with excellent crosslinkability. .

2. Alkyl Substitution With ketone oxime  Process for preparing copolymer containing protected isocyanate derivative

The copolymer according to the present invention dissolves the derivative represented by the formula (1) and the initiator in a polymerization solvent, a conventional radical polymerization method for 2 to 24 hours at a temperature of 50 to 90 ℃ under an inert gas atmosphere such as nitrogen, argon, etc. The reaction can be carried out according to the present invention. If the reaction temperature is lower than 50 ° C, a problem occurs that the polymer is not formed, and if the reaction temperature exceeds 90 ° C, a problem occurs in heat resistance. If the reaction time is less than 2 hours, there is a problem that the molecular weight is not controlled, if more than 24 hours, a problem in productivity occurs.

The initiator is not particularly limited, but azobisisobutyronitrile (AIBN), azobisvaleronitrile (AIVN), benzoyl peroxide (BPO) or di-t-butyl, which is a thermal polymerization initiator known as a radical polymerization initiator. One kind or two or more kinds selected from the group consisting of oxides (DTBP) may be used. Although it does not specifically limit as said polymerization solvent, 1 type, or 2 or more types chosen from the group which consists of dioxane, tetrahydrofuran, or benzene which are aromatic solvents can be used.

The copolymer according to the present invention may be prepared by further dissolving one or two or more kinds selected from the structural units represented by Chemical Formulas 2 to 4 together with the derivative in the polymerization solvent.

In the present invention, by adjusting the weight ratio between the monomer and the polymerization solvent or by controlling the amount of the radical initiator, it is possible to produce a copolymer of the appropriate molecular weight required in the semiconductor exposure process.

In more detail, the production method may be prepared by dissolving 0.1 to 10 moles of the initiator in 1 to 50 moles of the polymerization solvent with respect to 1 mole of the derivative represented by Chemical Formula 1.

When the initiator is contained in an amount of 0.1 to 10 moles with respect to 1 mole of the derivative represented by Chemical Formula 1, there is an advantage in that the reaction time can be easily adjusted. When the polymerization solvent is contained in an amount of 1 to 50 moles with respect to 1 mole of the derivative represented by Chemical Formula 1, there is an advantage of excellent meltability.

In addition, with respect to 1 mole of the derivative, 0.1 to 15 moles of any one or a plurality of structural units represented by Formulas 2 to 4 may be further dissolved in the polymerization solvent.

When any one or a plurality of monomers represented by Formulas 2 to 4 are contained in an amount of 0.1 to 15 moles with respect to 1 mole of the derivative represented by Formula 1, there is an advantage of increasing the polymerization yield.

The molecular weight of the copolymer of Structural Formula 1 is controlled to adjust the polymerization conditions so that the weight average molecular weight measured using gel permeation chromatography (GPC) is in the range of 5,000 to 100,000. If the molecular weight is 5,000 to 100,000, there is an advantage that the coating thickness can be easily adjusted.

Among the polymers obtained by the same method as described above, a polymer having a molecular weight having an appropriate coating ability is used as the antireflection film material.

3. Organic Antireflection film  Composition

The organic antireflection film composition according to the present invention includes the copolymer and the organic solvent.

Although the organic solvent is not particularly limited, propylene glycol monomethyl ether acetate (PGMEA), ethyl 3-ethoxy propionate, ethyl lactate, methyl 3-methoxy propionate or cyclo, which is a solvent for semiconductor microcircuit processing processes It is preferable that it is excellent in the film-forming ability like 1 type, or 2 or more types chosen from the group which consists of hexanone.

The composition is preferably contained in the organic anti-reflective coating composition in 0.1 to 20% by weight of the copolymer and 80 to 99.9% by weight of the organic solvent relative to the total weight of the composition.

When the copolymer is contained in an amount of 0.1 to 20% by weight, there is an advantage in that crosslinkability and optical properties are good. When the organic solvent is contained in an amount of 80 to 99.9% by weight, there is an advantage in that the antireflection film thickness can be easily adjusted.

The copolymer may further include an additive, and the additive is not particularly limited, and a thermal crosslinking agent, a thermal acid generator, or a mixture thereof may be used. The thermal crosslinking agent is not particularly limited, but melamine-formaldehyde resin, benzoguanine-formaldehyde resin, glycoluril-formaldehyde resin, urea-formaldehyde resin, phenolic resin, benzyl alcohol, epoxy compound, isocyanate or alkoxy methyl It may be one kind or two or more kinds selected from the group consisting of melamine. The thermal acid generator is not particularly limited, but may be selected from other strong protic acids such as one or two or more selected from the group consisting of p-toluenesulfonic acid, phosphoric acid, phthalic acid, oxalic acid or dodecylbenzenesulfonic acid.

The additive is contained in 0.001 to 10% by weight relative to the total weight of the composition, if contained in 0.001 to 10% by weight, there is an advantage that the pattern is formed vertically well.

The composition for organic antireflective coating of the present invention is preferably prepared by dissolving the copolymer in an organic solvent and then adding an additive.

4. Organic Antireflection film  Organic with the composition Antireflection film

The organic antireflective coating composition is filtered in a fine particle filtration apparatus, spun coated on a silicon wafer, and crosslinked at an appropriate temperature to obtain a desired antireflective coating. The anti-reflection film prepared in this manner serves to remove the problems caused by the reflection of light in the short wavelength far ultraviolet microcircuit processing process, so that the semiconductor device can be produced smoothly.

The alkyl-substituted ketone oxime-protected isocyanate cross-linked antireflective coating composition according to the present invention exhibits excellent performance as an organic antireflective coating for forming a microcircuit in an exposure wavelength region of short wavelength far ultraviolet rays of 248 nm, 193 nm and 157 nm. In addition, since it has superior adhesiveness and crosslinkability compared to the anti-reflection film based on the conventional hydroxy crosslinked groups, it has been found to be useful for the formation of ultrafine circuits when forming semiconductor devices.

Hereinafter, the present invention will be described in detail through examples. However, the embodiments are only illustrative of the present invention, and the scope of the present invention is not limited thereto.

Example  One: With methyl ethyl ketone oxime  Protected isocyanate monomers ( MEKOI ) Synthesis

<Scheme 1>

In a 500 ml round bottom flask equipped with a reflux condenser was placed 2-isocyanate ethyl methacrylate (Formula 5) (100.00 g, 0.64 mol) and butane 2-one oxime (Formula 6) (55.68 g, 0.64 mol), It was dissolved in 150 ml of pyridine and reacted at 40 ° C. for 2 hours. After the reaction, the resultant light yellow liquid product was obtained, and the unreacted product was separated and purified by silica gel column, followed by pure methyl ethyl ketone oxime-protected isocyanate (2- (0- [1'-Methylpropylideneamino] carboxyamino) ethylmethacrylate, The following formula "MEKOI" was recovered. 128.70 g (82.6% yield) was obtained and the breaking point was 139 ° C.

Example  2: Synthesis of Binary Copolymer Using Monomers of Formulas 4 and 7

Into the polymerization vessel, put anthracene methyl methacrylate (Formula 4) monomer (hereinafter referred to as "AMMA", 10.22g, 36mmol), MEKOI (Formula 7) monomer (17.44g, 72mmol) and 3 moles of AIBN, a radical initiator, dioxane (50ml ), Followed by polymerization at a polymerization temperature of 60 DEG C for 10 hours under a nitrogen atmosphere. The polymerization reaction was precipitated in excess methanol, and then filtered and dried to synthesize P (MEKOI / AMMA), a binary copolymer. The yield of P (MEKOI / AMMA) obtained was 84%, with data and graphs showing the GPC results for the polymer attached to FIG. 1.

Example  3: using monomers represented by the formulas (3), (4) and (7) Terpolymer  synthesis

Methyl methacrylate monomer (hereinafter referred to as “MMA”, 7.21 g, 72 mmol), anthracene methylmethacrylate (formula 4) monomer (hereinafter referred to as “AMMA”, 10.22 g, 36 mmol) in the polymerization vessel; MEKOI (Formula 7) monomer (8.72g, 36mmol) and 3 mol of AIBN as a radical initiator were added and dissolved in dioxane (50ml), and then polymerized at a polymerization temperature of 60 ℃ under nitrogen atmosphere for 10 hours. The polymerization reaction was precipitated in excess methanol, and then filtered and dried to synthesize P (MEKOI / MMA / AMMA), a terpolymer. The yield of P (MEKOI / MMA / AMMA) obtained was 87% and data and graphs showing the GPC results for the polymer were attached to FIG. 2.

Example  4: using monomers represented by the formulas (2), (3), (4) and (7) Employee Copolymer  synthesis

Hydroxyethylmaleimide (Formula 2) monomers (hereinafter referred to as "HEMI", 5.08 g, 36 mmol), methyl methacrylate (Formula 3) monomers (hereinafter referred to as "MMA", 7.21 g, 72 mmol), Anthracene methylmethacrylate (Formula 4) monomer (hereinafter referred to as "AMMA", 10.22g, 36mmol), MEKOI (Formula 7) monomer (8.72g, 36mmol) and AIBN 3mol radical initiator dissolved in dioxane (50ml) After the polymerization, the polymerization was carried out at a polymerization temperature of 60 ° C. for 10 hours under a nitrogen atmosphere. The polymerization reaction was precipitated in excess methanol, and then filtered and dried to synthesize P (MEKOI / HEMI / MMA / AMMA). The yield of P (MEKOI / HEMI / MMA / AMMA) obtained was 88%, with data and graphs showing the GPC results for the polymer attached to FIG. 3.

Example  5 to 7 and comparison 1: organic Antireflection film  Preparation of the composition

To prepare a composition according to the components and composition ratios described in Table 1 below. In more detail, the copolymer was dissolved in a solvent, stirred by adding a thermal crosslinking agent and a thermal acid generator, and filtered through a microporous membrane filter to prepare an organic antireflective coating composition.

Copolymer (% by weight) Thermal crosslinking agent (% by weight) Thermal acid generator (wt%) Solvent (% by weight) Example 5 a-1 4.5 b-1 One c-1 0.1 d-1 94.4 Example 6 a-2 4.5 b-1 One c-1 0.1 d-1 94.4 Example 7 a-3 4.5 b-1 One c-1 0.1 d-1 94.4 Comparative Example 1 a-4 4.5 b-1 One c-1 0.1 d-1 94.4

a-1: the copolymer prepared in Example 2

a-2: copolymer prepared in Example 3

a-3: copolymer prepared in Example 4

a-4: hydroxy type crosslinking group containing copolymer

b-1: Benzoguanamine-formaldehyde resin system

c-1: p-toluenesulfonic acid system

d-1: propylene glycol monomethyl ether acetate

Test Example  1: organic Antireflection film  Formation of the composition

The organic antireflective coating compositions of Examples 5 to 7 and Comparative Example 1 were spin-coated on a silicon wafer, and crosslinked at 100 ° C. to 250 ° C. for 10 to 120 seconds to prevent intermixing with photoresist to be formed in a later step. I was. Thereafter, the photoresist was spin-coated on the cured organic antireflection film, and soft baked at 80 ° C. or 120 ° C. for 30 to 120 seconds to remove the remaining solvent, followed by exposure through a 100 nm photomask, and 2.38 wt% tetramethyl. After the development process for 20 to 100 seconds using an alkaline developer such as ammonium hydroxide (TMAH), the results as shown in Table 2 are described.

Undercutting Putting CD change of pattern Example 5 ○ ○ 130 nm Example 6 ○ ◎ 120 nm Example 7 ◎ ◎ 100 nm Comparative Example 1 × × 250 nm

◎: Very good ○: Excellent △: Normal ×: Poor

Referring to Table 2, the organic anti-reflective coating including the organic anti-reflective coating composition of Examples 5 to 7 formed an acid equilibrium with the photoresist during development after the exposure process, so that the undercutting or footing was performed at the bottom of the photoresist micropattern. Footing) was not formed and the change of the dimensional pattern of the microcircuit due to the diffuse reflection was also very small, making it easy to form a high resolution microcircuit of 60 nm to 150 nm.

1 shows GPC results for an organic antireflective polymer prepared according to a second embodiment of the present invention.

2 shows the GPC results for the organic antireflection film polymer prepared according to the third embodiment of the present invention.

3 shows the GPC results for the organic antireflective polymer prepared according to the fourth embodiment of the present invention.

Claims (15)

An isocyanate derivative protected with an alkyl-substituted ketone oxime represented by the following formula (1) and a structural unit represented by the following formulas (2) to (4) as a comonomer, the weight average molecular weight of 5,000 for a semiconductor microcircuit exposure process Copolymer for organic antireflective coating of from 100,000 to 100,000: <Formula 1>

<Formula 2>

<Formula 3>

<Formula 4>

In Chemical Formulas 1 to 4, R and R ₁ are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkoxyalkyl group, a hydroxyalkyl group or a halogenated alkyl group, R ₂ is an alkyl group having 1 to 6 carbon atoms, R ₃ is hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group, a hydroxyalkyl group or a halogenated alkyl group, R ₄ and R ₅ are each independently hydrogen or methyl, R ₆ is hydrogen or methyl x represents a natural number of 1 to 6, In the copolymer, the mole fractions of the structural units represented by Chemical Formulas 1 to 4 are k, l, m and n, respectively, based on the total mole fraction of the structural unit, k is 0.1 to 0.7, l is 0 to 0.4, and m is 0.1-0.7, n is 0.1-0.4. delete A derivative represented by the following Chemical Formula 1, a structural unit represented by the following Chemical Formulas 2 to 4 and an initiator are dissolved in a polymerization solvent, Method for preparing a copolymer having a weight average molecular weight of 5,000 to 100,000 characterized in that the reaction in accordance with the radical polymerization method for 2 to 24 hours at a temperature of 50 to 90 ℃ under an inert gas atmosphere: <Formula 1>

<Formula 2>

<Formula 3>

<Formula 4>

In Chemical Formulas 1 to 4, R and R ₁ are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkoxyalkyl group, a hydroxyalkyl group or a halogenated alkyl group, R ₂ is an alkyl group having 1 to 6 carbon atoms, R ₃ is hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group, a hydroxyalkyl group or a halogenated alkyl group, R ₄ and R ₅ are each independently hydrogen or methyl, R ₆ is hydrogen or methyl x represents a natural number of 1 to 6, In the copolymer, the mole fractions of the structural units represented by Chemical Formulas 1 to 4 are k, l, m and n, respectively, based on the total mole fraction of the structural unit, k is 0.1 to 0.7, l is 0 to 0.4, and m is 0.1-0.7, n is 0.1-0.4. The method according to claim 3, For 1 mole of the derivative represented by Formula 1, 0.1 to 10 mol of the initiator is dissolved in 1 to 50 mol of the polymerization solvent, the weight average molecular weight of 5,000 to 100,000 method for producing a copolymer. The method according to claim 3, The polymerization solvent is a method of producing a copolymer having a weight average molecular weight of 5,000 to 100,000, characterized in that at least one selected from the group consisting of dioxane, tetrahydrofuran or methyl ethyl ketone. The method according to claim 3, The initiator is selected from the group consisting of azobisisobutyronitrile (AIBN), di-t-butyloxide (DTBP), acetyl peroxide (APO), benzoyl peroxide (BPO) or azobisvaleronitrile (AIVN). Method for producing a copolymer having a weight average molecular weight of 5,000 to 100,000 characterized in that one or more selected. delete The method according to claim 3, For 1 mole of the derivative represented by Formula 1, Method for producing a copolymer having a weight average molecular weight of 5,000 to 100,000 characterized by dissolving 0.1 to 15 moles of the structural units represented by Formulas 2 to 4 in the polymerization solvent. Copolymers according to claim 1; And An organic antireflective coating composition comprising an organic solvent. The method according to claim 9, In terms of the total weight of the composition, 0.1 to 20% by weight of the copolymer; And An organic antireflection film composition comprising 80 to 99.9% by weight of the organic solvent. The method according to claim 9, The organic solvent is butyrolactone, cyclopentanone, cyclohexanone, dimethyl acetamide, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate or ethyl lac Organic antireflection film composition, characterized in that one or two or more selected from the group consisting of tate. The method according to claim 9, The organic antireflective coating composition further comprises an additive. The method according to claim 12, The additive is an organic antireflection film composition, characterized in that the thermal crosslinking agent, a thermal acid generator or a mixture thereof. The method according to claim 12, An organic antireflection film composition comprising the additive in an amount of 0.001 to 10% by weight based on the total weight of the composition. An organic antireflection film produced by the organic antireflection film composition according to claim 9.

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