KR20020059261A - Organic anti-reflective polymer and preparation thereof - Google Patents

Abstract

The present invention is to prevent the reflection of the lower layer layer in the ultra-fine pattern forming process using a photoresist for lithography using 248 nm KrF, 193 nm ArF and 157 nm F ₂ laser during the semiconductor device manufacturing process and to prevent the reflection of ArF light and photoresist itself. The present invention relates to an organic anti-reflective compound capable of removing standing waves in the change in thickness and a method for synthesizing the same, and the present invention also relates to an anti-reflective composition containing such an organic anti-reflective compound, an anti-reflective film using the same, and a method for producing the same. When the compound according to the present invention is used as an anti-reflection film in an ultra-fine pattern forming process in a semiconductor manufacturing process, it eliminates CD fluctuations resulting from standing waves, reflections and underlying films due to variations in optical properties and resist thickness of the underlying film layer on the wafer. As a result, stable ultrafine patterns of 64M, 256M, 1G, 4G, and 16G DRAMs can be formed, thereby increasing product yield.

Description

Organic antireflective compound and preparation method therefor {ORGANIC ANTI-REFLECTIVE POLYMER AND PREPARATION THEREOF}

The present invention prevents the reflection of the lower layer layer and the thickness of the light and photoresist itself in the ultrafine pattern formation process using the photoresist for lithography using 248 nm KrF, 193 nm ArF and 157 nm F ₂ laser during the semiconductor device manufacturing process. The present invention relates to an antireflection organic material capable of removing standing waves due to change. More specifically, the present invention relates to an organic anti-reflective compound that can be used in forming ultrafine patterns of 64M, 256M, 1G, and 4G DRAM, and a method of manufacturing the same. The present invention also relates to an anti-reflective composition containing such an organic anti-reflective compound, an anti-reflection film using the same, and a method of manufacturing the same.

In the ultra-fine pattern formation process of the semiconductor manufacturing process, CD (critical dimension) by standing wave, reflective notching due to the optical property of the lower layer on the wafer and variation of the thickness of the photoresist layer, diffracted light from the lower layer and reflected light ) Inevitably occurs. Therefore, the introduction of a film layer capable of preventing reflection in the lower film layer by introducing an organic material that absorbs light well in the wavelength range of light used as an exposure source has been proposed, and this film is an antireflection film.

The antireflection film is classified into an inorganic antireflection film and an organic antireflection film according to the type of material used largely, or is classified into an absorption antireflection film and an interferometer antireflection film according to a mechanism. In the pattern formation process using I-line of 365 nm wavelength, inorganic antireflection film is mainly used, TiN and amorphous carbon (Amorphous C) are used as an absorption system, and SiON is mainly used as an interferometer.

In the ultrafine pattern formation process using KrF light, SiON has been mainly used as an inorganic type, but efforts to use an organic compound in an antireflection film have been continued in recent years. In light of the trends to date, most of the organic anti-reflective coatings must satisfy the following basic conditions.

(1) During the application of the process, the photoresist should not be dissolved and peeled off by the solvent. To this end, the molded film must be designed to achieve a crosslinked structure, and chemicals should not be generated as a by-product.

(2) There should be no entry of chemicals such as acids or amines from the antireflection film. If the acid is migrated from the anti-reflection film, undercutting occurs at the bottom of the pattern, and bases such as amines tend to cause footing phenomenon.

(3) The anti-reflection film should have a relatively high etching rate compared to the upper photoresist film, so that the etching process can be performed smoothly using the photoresist film as a mask during etching.

(4) The antireflection film should therefore be able to serve as a sufficient antireflection film with a thickness as thin as possible.

Meanwhile, a satisfactory anti-reflection film has not been developed in an ultrafine pattern forming process using ArF light. In the case of the inorganic antireflection film, a material for controlling the interference phenomenon at 193 nm, which is a light source, has not been announced yet, and efforts to use an organic antireflection film have been continued in recent years.

Therefore, in all photoresist films, it is necessary to use an organic anti-reflective material having a high absorption at a specific wavelength in order to prevent standing waves and reflections generated during exposure and to remove the influence of back diffraction and reflected light from the lower layer. It is an urgent task.

Accordingly, an object of the present invention is to provide a novel organic compound that can be used as an antireflection film in an ultrafine pattern forming process using 193 nm ArF and 248 nm KrF light during a semiconductor device manufacturing process.

It is still another object of the present invention to provide a method for producing an organic compound capable of preventing diffuse reflection.

Still another object of the present invention is to provide an anti-reflective composition containing the compound for preventing anti-reflection and a manufacturing method thereof.

Still another object of the present invention is to provide an antireflection film formed using such an antireflection composition, a method of forming the same, and a semiconductor device manufactured using the same.

In the present invention, the compound itself contains a chromophore having a high absorbance to absorb at 193 nm and 248 nm wavelengths. In order to give formation, airtightness, and solubility of an organic antireflection film, a crosslinking reaction may occur during hard baking after coating. The crosslinking mechanism of the alcohol group and the functional period was introduced. In particular, the present invention has maximized the efficiency and storage stability of the crosslinking reaction, the anti-reflective coating resin of the present invention has excellent solubility in all solvents of the hydrocarbon system and has a solvent resistance that does not dissolve in any solvent during hard baking . Therefore, no problem occurs when the photoresist film is applied, and undercutting and footing do not occur when the pattern is formed. In particular, since it is formed of an acrylate-based polymer, it has an excellent etching rate compared to the photoresist film during etching. The selection ratio was improved.

In order to achieve the object of the present invention, the basic formula of the resin used as the organic anti-reflection film of the present invention is represented by the following formula (2) and (3).

In Formula 2, R _a , R _b , and R _c each represent a hydrogen or methyl group, and R ₁ to R _{9 each} represent hydrogen, hydroxy, methoxycarbonyl, carboxyl, hydroxymethyl, and C ₁ to C ₅ . Or unsubstituted linear or branched alkyl, alkoxyalkyl, w, x, y each represents 0.01 to 0.99 mole fraction, and n represents an integer of 1 to 3, respectively.

Also in Formula 3, R₁₁And R₁₂ Are branched or straight chain substituted C, respectively_One~ C₁₀Alkoxy group, R₁₂Represents hydrogen or a methyl group.

It is preferable to use the compound of Formula 3 selected from the group consisting of the following Chemical Formulas 4 to 7.

The compounds of Formulas 4 to 7 harden well in the presence of an acid and other compounds having alcohol groups.

The compound of Chemical Formula 2 may be prepared by polymerizing 9-anthralaldehyde oxime acrylate monomer, hydroxy alkyl acrylate monomer, and methyl methacrylate with an initiator in a solvent, wherein each monomer is 0.01 to 0.99 It has a mole fraction ratio.

The initiator that can be used to prepare the compound of Formula 2 according to the present invention may be used a general radical initiator, preferably 2,2-azobisisobutyronitrile (AIBN), acetyl peroxide, lauryl per Oxide, t-butylperoxide may be selected from the group consisting of, a solvent used may be a general organic solvent, preferably a group consisting of tetrahydrofuran, toluene, benzene, methyl ethyl ketone or dioxane The selected one can be used.

In the method for preparing the compound of Formula 2 according to the present invention, the reaction temperature is preferably performed at 50 to 90 ° C.

The method of preparing the compound of Formula 3 consists of polymerizing (meth) acrolein to prepare poly (meth) acrolein, and then reacting the resultant with alkyl alcohol having 1 to 10 carbon atoms, which are branched or main chain substituted.

More specifically, first, (meth) acrolein is dissolved in an organic solvent, and a polymerization initiator is added thereto, followed by polymerization for 4 to 6 hours at a temperature of 60 to 70 ° C. under vacuum, followed by side chain or The main chain substituted alkyl alcohol having 1 to 10 carbon atoms is reacted with trifluoromethylsulfonic acid as a catalyst at room temperature for 20 to 30 hours.

In the above process, the organic solvent is one or more selected from the group consisting of tetrahydrofuran (THF), cyclohexanone, dimethylformamide, dimethyl sulfoxide, dioxane, methyl ethyl ketone, benzene, toluene and xylene It is preferable to mix and use.

In addition, the polymerization initiator is 2,2-azobisisobutyronitrile (AIBN), benzoyl peroxide, acetyl peroxide, lauryl peroxide, t- butyl per acetate, t- butyl hydroperoxide and di- t- butyl Preference is given to using those selected from the group consisting of peroxides.

In addition, the alkyl alcohol having 1 to 10 carbon atoms is preferably methanol or ethanol.

The present invention provides a composition for an anti-reflection film comprising a compound according to the formula (2). The present invention also provides a composition for anti-reflection film comprising one of the compound of Formula 2 and the compound of Formula 3. In addition, the present invention provides an anti-reflection film composition, characterized in that additionally added one or two or more additives selected from the group consisting of anthracene derivatives to the composition for an anti-reflection film.

Anthracene derivatives as the additives include anthracene, 9-anthracenemethanol, 9-anthracenecarbonitrile, 9-anthracenecarboxylic acid, ditranol, 1,2,10-anthracentriol, anthraflavonic acid, 9-anthaldehyde oxime, 9- Anthaldehyde, 2-amino-7-methyl-5-oxo-5H- [1] benzopyrano [2,3-b] benzopyridine-3-carbonitrile, 1-aminoanthraquinone, anthraquinone-2- Carboxylic acid, 1,5-dihydroxyanthraquinone, anthrone, 9-anthryltrifluoromethylketone, 9-alkylanthracene derivative of formula (8), carboxyl anthracene derivative of formula (9), carboxyl of formula (10) Preference is given to those selected from the group consisting of anthracene derivatives.

In the above formula

R ₁ , R ₂ and R ₃ are hydrogen, a hydroxy group or a substituted or unsubstituted straight or branched chain alkyl or alkoxyalkyl having 1 to 5 carbon atoms, respectively.

The present invention provides a method for preparing an anti-reflection film formed by mixing the compound of Chemical Formula 2 and the compound of Chemical Formula 3, dissolving it in an organic solvent, filtering the solution, and applying the solution to a lower layer, followed by hard baking. The compound of Formula 3 and the compound of Formula 3 is dissolved in an organic solvent, and then a solution in which one or two or more additives selected from the group consisting of anthracene derivatives is filtered and applied to the lower layer, followed by hard baking. To provide.

In the production method of the anti-reflection film, the organic solvent in the polymerization reaction may be used a conventional organic solvent, preferably ethyl 3-ethoxy propionate, methyl 3-methoxy propionate, cyclohexanone, Propylene glycol methyl ether acetate and the like can be used. At this time, the amount of the solvent is preferably 200 to 5000% by weight.

In addition, the hard bake is preferably performed at a temperature of 100 to 300 ° C. for 10 to 1000 seconds, and crosslinks the antireflection film resin through the hard bake to form an antireflection film.

The antireflection film formed by the above method was found to show excellent performance as an organic antireflection film in the ultrafine pattern formation process using 193 nm ArF, 248 nm KrF and 157 nm F ₂ laser.

The present invention also provides a semiconductor device manufactured using the antireflection film manufactured by the above method.

Hereinafter, the present invention will be described in more detail. However, this embodiment is not intended to limit the scope of the present invention, but is presented by way of example only.

Example 1 Synthesis of Poly [9-anthralaldehyde oxime acrylate- (2-hydroxyethyl acrylate) -methyl methacrylate] copolymer

(1) Synthesis of 9-anthralaldehyde oxime acrylate

0.5 mole of 9-anthralaldehyde oxime and 0.5 mole of pyridine were dissolved in tetrahydrofuran and 0.5 mole of acryloyl chloride was added thereto. The reaction solution was filtered and extracted again with ethyl acetate, washed several times with distilled water and dried using a distillation under reduced pressure to obtain 9-anthralaldehyde oxime acrylate represented by the following formula (11). At this time, the yield was 82%.

(2) Synthesis of Poly [9-anthralaldehyde oxime acrylate- (2-hydroxyethyl acrylate) -methyl methacrylate] copolymer

0.3 g of the 9-anthralaldehyde oxime acrylate monomer, 0.5 mole of 2-hydroxyethyl acrylate, and 0.2 mole of methyl methacrylate were added to a 500 ml round bottom flask, and 300 g of tetrahydrofuran (THF) prepared in advance was thoroughly added while stirring. When mixed, 0.1 g-3 g of 2.2'-azobisisobutylonitrile (AIBN) was added thereto, and the mixture was reacted at 60 ° C to 75 ° C for 5-20 hours under a nitrogen atmosphere. After completion of the reaction, the solution was precipitated in ethyl ether or normal nucleic acid solvent, filtered and dried to obtain a poly [9-anthralaldehyde oxime acrylate- (2-hydroxyethyl) having a structure represented by the following formula (19). Acrylate) -methyl methacrylate] resin was obtained. At this time, the yield was 79%.

Example 2 Synthesis of Poly [9-anthralaldehyde oxime acrylate- (3-hydroxypropyl acrylate) -methyl methacrylate] copolymer

0.3 mol of 9-anthralaldehyde oxime acrylate monomer synthesized in Example 1, 0.5 mol of 3-hydroxypropyl acrylate and 0.2 mol of methyl methacrylate were put into a 500 ml round bottom flask and prepared with tetrahydrofuran (THF). ) 300 g was added and 0.1 g-3 g of 2.2'-azobisisobutylonitrile (AIBN) was added thereto, followed by reaction for 5-20 hours at a temperature of 60 ° C. to 75 ° C. under a nitrogen atmosphere. After completion of the reaction, the solution was precipitated in ethyl ether or normal nucleic acid solvent, filtered and dried to obtain a poly [9-anthralaldehyde oxime acrylate- (3-hydroxypropyl) having a structure represented by the following formula 20 as a compound according to the present invention. Acrylate) -methyl methacrylate] resin was obtained. At this time, the yield was 809%.

Example 3 Synthesis of Poly [9-anthralaldehyde oxime acrylate- (4-hydroxybutyl acrylate) -methyl methacrylate] copolymer

0.3 mol of 9-anthralaldehyde oxime acrylate monomer synthesized in Example 1, 0.5 mol of 2-hydroxyethyl acrylate and 0.2 mol of methyl methacrylate were put into a 500 ml round bottom flask and prepared with tetrahydrofuran (THF). ) 300 g was added and 0.1 g-3 g of 2.2'-azobisisobutylonitrile (AIBN) was added thereto, followed by reaction for 5-20 hours at a temperature of 60 ° C. to 75 ° C. under a nitrogen atmosphere. After completion of the reaction, the solution was precipitated in ethyl ether or normal nucleic acid solvent, filtered and dried to obtain a poly [9-anthralaldehyde oxime acrylate- (4-hydroxybutyl) having a structure represented by the following formula (21) according to the present invention. Acrylate) -methyl methacrylate] resin was obtained. At this time, the yield was 80%.

Example 4 Synthesis of Poly [9-anthralaldehyde oxime methacrylate- (2-hydroxyethylacrylate) -methylmethacrylate] copolymer

(1) Synthesis of 9-anthralaldehyde oxime methacrylate

0.5 mole of 9-anthracenealdehyde oxime and 0.5 mole of pyridine were dissolved in tetrahydrofuran and 0.5 mole of methacryloyl chloride was added. The reaction solution was filtered and extracted again with ethyl acetate, washed several times with distilled water and dried using a distillation under reduced pressure to obtain 9-anthralaldehyde oxime methacrylate represented by the following formula (15). At this time, the yield was 80%.

(2) Synthesis of poly [9-anthralaldehyde oxime methacrylate- (2-hydroxyethyl acrylate) -methyl methacrylate] copolymer

0.3 g of the 9-anthralaldehyde oxime methacrylate monomer, 0.5 mol of 2-hydroxyethyl acrylate, and 0.2 mol of methyl methacrylate were added to a 500 ml round bottom flask, and 300 g of tetrahydrofuran (THF) prepared in advance was added while stirring. When completely mixed, 0.1g-3g of 2.2'-azobisisobutylonitrile (AIBN) was added thereto, followed by reaction for 5-20 hours at a temperature of 60 ° C to 75 ° C under a nitrogen atmosphere. After completion of the reaction, the solution was precipitated in ethyl ether or normal nucleic acid solvent, filtered and dried to obtain a poly [9-anthralaldehyde oxime methacrylate- (2-hydroxy) having a structure represented by the following formula (22) according to the present invention. Ethyl acrylate) -methyl methacrylate] resin. At this time, the yield was 79%.

Example 5 Synthesis of Poly [9-anthralaldehyde oximemethacrylate- (3-hydroxypropylacrylate) -methylmethacrylate] copolymer

Tetrahydrofuran prepared in advance by stirring 0.3 mole of 9-anthralaldehyde oxime methacrylate monomer synthesized in Example 4, 0.5 mole of 3-hydroxypropyl acrylate and 0.2 mole of methyl methacrylate into a 500 ml round bottom flask ( THF) 300g and completely mixed, 0.1g-3g of 2.2'-azobisisobutylonitrile (AIBN) was added and reacted for 5-20 hours at 60 ℃ to 75 ℃ temperature under a nitrogen atmosphere. After completion of the reaction, the solution was precipitated in ethyl ether or normal nucleic acid solvent, filtered and dried to obtain a poly [9-anthralaldehyde oxime methacrylate- (3-hydroxy) having a structure represented by the following formula (23) according to the present invention. Propyl acrylate) -methyl methacrylate] resin was obtained. At this time, the yield was 80%.

Example 6 Synthesis of Poly [9-anthralaldehyde oxime methacrylate- (4-hydroxybutyl acrylate) -methyl methacrylate] copolymer

0.3 mol of 9-anthralaldehyde oxime methacrylate monomer synthesized in Example 4, 0.5 mol of 4-hydroxybutyl acrylate, and 0.2 mol of methyl methacrylate were added to a 500 ml round bottom flask and prepared with pre-prepared tetrahydrofuran ( THF) 300g was added, 0.1g-3g of 2.2'-azobisisobutylonitrile (AIBN) was completely mixed and reacted for 5-20 hours at a temperature of 60 ° C to 75 ° C under a nitrogen atmosphere. After completion of the reaction, the solution was precipitated in ethyl ether or normal nucleic acid solvent, filtered and dried to obtain a poly [9-anthralaldehyde oxime methacrylate- (4-hydroxy) having a structure represented by the following formula 24, which is a compound according to the present invention. Butyl acrylate) -methyl methacrylate] resin was obtained. At this time, the yield was 78%.

Example 7 Synthesis of Poly [Acroleindimethylacetal] Resin

100 g of acrolein, 66 g of tetrahydrofuran (THF), and 2 g of AIBN were placed in a 500 ml round-bottom flask, vacuumed, and reacted at 65 ° C. for 5 hours. After filtering, the white solid (polyacrolein) produced was filtered and ethyl Wipe several times with ether. At this time, the yield was 80%. 80 g of the white solid and 500 g of methanol were put in a 1000 ml round bottom flask, followed by 1 ml of trifluoromethylsulfonic acid as a catalyst, followed by reaction at room temperature (25 ° C.) for at least 24 hours. Initially insoluble white solids (polyacrolein) are dissolved in methanol as the reaction is completed. After completion of the reaction, confirm that the absorption band of 1690cm ^-1 disappeared from the infrared absorption spectrometer (IR spectrum), neutralize with triethylamine, remove methanol with a distillation to make it thick, and precipitate in distilled water and vacuum-dry to obtain the precipitate. A compound of formula 4 was obtained. At this time, the yield was 65%. [Molecular weight 6,820; Polydispersity 1.60; 1 H NMR 1.2-2.1 ppb (3H), 3.0-3.8 ppb (6H), 3.8-4.7 (1H)]

Example 8 Synthesis of Poly [Acrolein Diethyl Acetal] Resin

100 g of acrolein, 66 g of THF, and 2 g of AIBN were placed in a 500 ml round-bottom flask, vacuumed, and reacted at 65 ° C. for 5 hours. After filtering, the white solid (polyacrolein) was filtered and washed several times with ethyl ether. . At this time, the yield was 80%. 80 g of the white solid and 500 g of ethanol were put into a 1000 ml round bottom flask, followed by 1 ml of trifluoromethylsulfonic acid as a catalyst, followed by reaction at room temperature (25 ° C.) for at least 24 hours. Initially insoluble white solids (polyacrolein) are dissolved in methanol as the reaction is completed. After completion of the reaction, confirm that the absorption band of 1690cm ^-1 disappears from the infrared absorption spectrometer (IR spectrum), neutralize with triethylamine, remove ethanol with a distillation to make it thick, and then precipitate in distilled water and vacuum-dry to obtain the precipitate. A compound of formula 5 was obtained. At this time, the yield was 60%. [Molecular weight 7,010; Polydispersity 1.78; 1 H NMR 1.2-2.1 ppb (9H), 3.0-3.8 ppb (4H), 3.8-4.7 (1H)]

Example 9 Synthesis of Poly [Metacrolein Dimethyl Acetal] Resin

100 g of methacrolein, 66 g of THF, and 2 g of AIBN were placed in a 500 ml round-bottom flask, vacuumed, and reacted at 65 ° C. for 5 hours. After completion of the reaction, the produced white solid (polymethcrolein) was filtered and then ethyl ether Wipe several times with. 80 g of the white solid and 500 g of methanol were placed in a 1000 ml round bottom flask, followed by 1 ml of trifluoromethylsulfonic acid as a catalyst, followed by reaction at room temperature (25 ° C.) for at least 24 hours. Initially insoluble white solids (polyacrolein) are dissolved in methanol as the reaction is completed. After completion of the reaction, confirm that the absorption band of 1690cm ^-1 disappeared from the infrared absorption spectrometer (IR spectrum), neutralize with triethylamine, remove methanol with a distillation to make it thick, and precipitate in distilled water and vacuum-dry to obtain the precipitate. A compound of formula 6 was obtained. At this time, the yield was 65%. [Molecular weight 6,800; Polydispersity 1.63; 1 H NMR 1.2-2.1 ppb (5H), 3.0-3.8 ppb (6H), 3.8-4.7 (1H)]

Example 10 Synthesis of Poly [Metacrolein Diethyl Acetal] Resin

100 g of methacrolein, 66 g of THF, and 2 g of AIBN were placed in a 500 ml round-bottom flask, vacuumed, and reacted at 65 ° C. for 5 hours. After completion of the reaction, the produced white solid (polymethcrolein) was filtered and then ethyl ether Wipe several times with. 80 g of the white solid and 500 g of ethanol were put into a 1000 ml round bottom flask, followed by 1 ml of trifluoromethylsulfonic acid as a catalyst, followed by reaction at room temperature (25 ° C.) for at least 24 hours. Initially insoluble white solids (polyacrolein) are dissolved in methanol as the reaction is completed. After completion of the reaction, confirm that the absorption band of 1690cm ^-1 disappears from the infrared absorption spectrometer (IR spectrum), neutralize with triethylamine, remove ethanol with a distillation to make it thick, and then precipitate in distilled water and vacuum-dry to obtain the precipitate. A compound of formula 7 was obtained. At this time, the yield was 61%. [Molecular weight 7,200; Polydispersity 2.0; 1 H NMR 1.2-2.1 ppb (11 H), 3.0-3.8 ppb (4 H), 3.8-4.7 (1 H)]

Example 11 Manufacture of Antireflection Film

The selected ones of the compounds prepared in Examples 1 to 6 were mixed with the selected ones of the compounds prepared in Examples 7 to 10 and dissolved in propylene glycol methyl ethyl acetate (PGMEA), and then the solution was used alone or in the solution. 0.1-30 wt% of an anthracene compound group as one additive was added to dissolve completely, and then the solution was filtered and applied to a wafer and hardbaked at 100-300 ° C for 10-1000 seconds. Thereafter, a photosensitive film was applied and a fine pattern forming process was performed.

As described above, the compounds having the basic structures of Chemical Formulas 1, 2, and 3 according to the present invention not only contain a chromophore having a high absorbance in the resin itself, but the antireflection film resin according to the present invention is soluble in all hydrocarbon solvents. Since it is excellent and does not dissolve in any solvent at the time of hard baking, it does not generate any problem at the time of application | coating of the photosensitive film | membrane, and shows the outstanding effect that undercutting and footing do not occur at the time of pattern formation.

In particular, since it is formed of an acrylate-based polymer has an excellent etching rate compared to the photosensitive film during etching has an effect that the etching selectivity is significantly improved.

Therefore, by using the compound according to the present invention as an anti-reflection film in the ultra-fine pattern forming process of the semiconductor manufacturing process, not only the reflection of the lower layer layer in the lithography process of the semiconductor manufacturing process but also the thickness of the light and photoresist itself By eliminating standing waves caused by the change, stable ultrafine patterns of 64M, 256M, 1G, 4G, and 16G DRAMs can be formed, thereby increasing the yield of products.

Claims (25)

Compound having a structure of formula (2). (Formula 2) Where R _a , R _b , R _c are each a hydrogen or methyl group, R ₁ to R ₉ are hydrogen, hydroxy, methoxycarbonyl, carboxyl, hydroxymethyl, C ₁ -C ₅ substituted or unsubstituted straight chain Or branched alkyl and alkoxyalkyl, w, x and y each represent 0.01 to 0.99 mole fraction, and n represents an integer of 1 to 3, respectively. The poly [9-] compound of claim 1, wherein R _a and R _c are each hydrogen, R _b is a methyl group, R ₁ to R ₉ are each hydrogen, w: x: y is 0.3: 0.2: 0.5, and n is 2; Anthralaldehyde oxime acrylate- (2-hydroxyethyl acrylate) -methyl methacrylate]. The poly [9-] compound of claim 1, wherein R _a and R _c are each hydrogen, R _b is a methyl group, R ₁ to R ₉ are each hydrogen, w: x: y is 0.3: 0.2: 0.5, and n is 3; Anthralaldehyde oxime acrylate- (3-hydroxypropyl acrylate) -methyl methacrylate]. The poly [9-] compound according to claim 1, wherein R _a and R _c are each hydrogen, R _b is a methyl group, R ₁ to R ₉ are each hydrogen, w: x: y is 0.3: 0.2: 0.5, and n is 4 Anthralaldehyde oxime acrylate- (4-hydroxybutyl acrylate) -methyl methacrylate]. The poly [9-anthralaldehyde according to claim 1, wherein R _a , R _b are methyl groups, R _c and R ₁ to R ₉ are each hydrogen, w: x: y is 0.3: 0.2: 0.5 and n is 2 Oxime methacrylate- (2-hydroxyethyl acrylate) -methyl methacrylate]. The poly [9-anthralaldehyde according to claim 1, wherein R _a , R _b are methyl groups, R _c and R ₁ to R ₉ are each hydrogen, w: x: y is 0.3: 0.2: 0.5 and n is 3 Oxime methacrylate- (3-hydroxypropyl acrylate) -methyl methacrylate]. The poly [9-anthralaldehyde according to claim 1, wherein R _a , R _b are methyl groups, R _c and R ₁ to R ₉ are each hydrogen, w: x: y is 0.3: 0.2: 0.5 and n is 4 Oxime methacrylate- (4-hydroxybutyl acrylate) -methyl methacrylate]. 9-Anthral aldehyde oxime acrylate monomer, hydroxyalkyl acrylate monomer and methyl methacrylate is a method for producing a compound of formula 2 characterized in that the polymerization with an initiator in a solvent. The method of claim 8, wherein the molar ratio of each monomer is 0.1 to 0.99: 0.1 to 0.99: 0.1 to 0.99. The method of claim 8, wherein the initiator is selected from the group consisting of 2,2-azobisisobutyronitrile (AIBN), acetyl peroxide, lauryl peroxide, t-butyl peroxide A process for preparing the compound of formula (2). The method of claim 8, wherein the solvent is selected from the group consisting of tetrahydrofuran, toluene, benzene, methylethylketone or dioxane. The method of claim 8, wherein the polymerization is performed at a temperature in a range of 50 ° C. to 90 ° C. 10. An antireflection film composition comprising the compound of formula (2). An antireflection film composition comprising a compound of Formula 2 and a compound of Formula 3 below. (Formula 3) R in the above formula₁₁And R₁₂ Are branched or straight chain substituted C, respectively_One~ C₁₀Alkoxy group, R₁₂Represents hydrogen or a methyl group. Including the compound of Formula 2 and the compound of Formula 3, anthracene, 9-anthracenemethanol, 9-anthracenecarbonitrile, 9-anthracenecarboxylic acid, dithranol, 1,2,10-anthracentriol, anthraflavonic acid , 9-anthaldehyde oxime, 9-anthralaldehyde, 2-amino-7-methyl-5-oxo-5H- [1] benzopyrano [2,3-b] benzopyridine-3-carbonitrile, 1- Aminoanthraquinone, anthraquinone-2-carboxylic acid, 1,5-dihydroxyanthraquinone, anthrone, 9-anthryltrifluoromethylketone, 9-alkylanthracene derivative of formula (8), carboxyl of formula (9) Anthracene derivative, anti-reflective coating composition characterized in that the addition of one or two or more compounds selected from the group consisting of carboxyl anthracene derivative of the formula (10). (Formula 8) (Formula 9) Formula 10 Where R ₁ , R ₂ and R ₃ are each independently hydrogen, hydroxy, alkyl, hydroxymethyl or C ₁ to C ₅ substituted or unsubstituted straight or branched chain alkyl or alkoxyalkyl. Dissolving the compound of Formula 2 and the compound of Formula 3 in an organic solvent, the solution is filtered and applied to the lower layer and then hard-baked, characterized in that the manufacturing method of the anti-reflection film. 17. The organic solvent according to claim 16, wherein the organic solvent is selected from the group consisting of ethyl 3-ethoxy propionate, methyl 3-methoxy propionate, cyclohexanone, and propylene glycol methyl ether acetate. A method for producing an antireflection film, characterized in that it is used in an amount of 200 to 5000% by weight. The method for producing an anti-reflection film according to claim 16, wherein the temperature during hard bake is 100 to 300 deg. After dissolving the compound of Formula 2 and the compound of Formula 3 in an organic solvent, anthracene, 9-anthracenemethanol, 9-anthracenecarbonitrile, 9-anthracenecarboxylic acid, ditranol, 1,2,10-anthracentriol, Anthraflavonic acid, 9-anthaldehyde oxime, 9-anthralaldehyde, 2-amino-7-methyl-5-oxo-5H- [1] benzopyrano [2,3-b] benzopyridine-3-carbonitrile , 1-aminoanthraquinone, anthraquinone-2-carboxylic acid, 1,5-dihydroxyanthraquinone, anthrone, 9-anthryltrifluoromethylketone, 9-alkylanthracene derivative of Formula 8, Formula 9 The method of manufacturing an anti-reflection film, characterized in that the carboxyl anthracene derivative of the formula, a carboxyl anthracene derivative of the formula (10) is added to the lower layer by filtering a solution to which one or two or more compounds are added is filtered. 20. The method according to claim 19, wherein the organic solvent is selected from the group consisting of ethyl 3-ethoxy propionate, methyl 3-methoxy propionate, cyclohexanone, and pyrophyllene glycol methyl ether acetate. A method for producing an antireflection film, characterized in that it is used in an amount of 200 to 5000% by weight of the antireflection film resin. 20. The method for producing an antireflection film according to claim 19, wherein the temperature during said hard bake is 100 to 300 deg. 20. The method of claim 19, wherein the additive is used in an amount of 0.1 to 30 wt%. A semiconductor device manufactured using the composition for antireflection film of claim 13. A semiconductor device manufactured using the composition for antireflection film of claim 14. A semiconductor device, which is manufactured using the composition for antireflection film of claim 15.