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WO2024147537A1 - Composition de résine pour film antireflet, film antireflet et dispositif d'imagerie à semi-conducteurs - Google Patents

Composition de résine pour film antireflet, film antireflet et dispositif d'imagerie à semi-conducteurs Download PDF

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Publication number
WO2024147537A1
WO2024147537A1 PCT/KR2023/021580 KR2023021580W WO2024147537A1 WO 2024147537 A1 WO2024147537 A1 WO 2024147537A1 KR 2023021580 W KR2023021580 W KR 2023021580W WO 2024147537 A1 WO2024147537 A1 WO 2024147537A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
resin composition
binder resin
group
reflection film
Prior art date
Application number
PCT/KR2023/021580
Other languages
English (en)
Korean (ko)
Inventor
김정식
남궁진웅
안보은
Original Assignee
동우 화인켐 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020230137665A external-priority patent/KR20240108782A/ko
Application filed by 동우 화인켐 주식회사 filed Critical 동우 화인켐 주식회사
Publication of WO2024147537A1 publication Critical patent/WO2024147537A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/22—Expanded, porous or hollow particles
    • C08K7/24—Expanded, porous or hollow particles inorganic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/02—Ingredients treated with inorganic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • H01L27/146—

Definitions

  • a solid-state imaging device is a device that converts an image captured through light energy into electrical information.
  • a microlens for light collection is formed on the photoelectric conversion device, and an anti-reflection film is formed on the surface. This anti-reflection film serves to prevent noise such as flare or ghost.
  • the average particle diameter of the hollow aluminosilicate particles may be 30 to 150 nm.
  • the hollow aluminosilicate particles may have a surface modified with a second binder resin having a thermosetting functional group and a hydrolyzable silyl group.
  • the second binder resin may include one or more repeating units represented by the following formulas 1 to 4 and a repeating unit represented by the following formula 5.
  • R 1 to R 5 are each independently a hydrogen atom or a methyl group
  • R 6 is a hydroxy group, an alkoxy group of C 1 -C 4 or a halogen
  • R 7 is a hydrogen atom or a C 1 -C 20 alkyl group
  • n is an integer from 1 to 3.
  • L 6 does not exist or is an alkylene group of C 1 -C 18 .
  • the second binder resin may have a molar ratio of one or more of the repeating units represented by Formulas 1 to 4 and the repeating unit represented by Formula 5 of 10:90 to 90:10.
  • the second binder resin may contain 1 to 50 mol% of the repeating unit represented by Formula 6 based on 100 mol% of the total repeating units constituting the binder resin.
  • the first binder resin may include one or more of the repeating units represented by the following formulas 1 to 4.
  • L 1 to L 4 each independently do not exist or are a C 1 -C 10 alkylene group or a C 1 -C 10 oxyalkylene group.
  • the first binder resin may include one or more of the repeating units represented by the following formulas 1 to 4 and a repeating unit represented by the following formula 5.
  • R 1 to R 5 are each independently a hydrogen atom or a methyl group
  • R 7 is a hydrogen atom or a C 1 -C 20 alkyl group
  • R 8 is a hydrogen atom or a methyl group
  • the first binder resin may have a molar ratio of one or more of the repeating units represented by Formulas 1 to 4 and the repeating unit represented by Formula 5 of 10:90 to 90:10.
  • the Si/Al molar ratio refers to the molar ratio of the silicon (Si) element in the hollow aluminosilicate particles and the aluminum (Al) element used for modification.
  • the Si/Al molar ratio is 7 to 15, preferably 7 to 12, as described above. If the Si/Al molar ratio is less than 7, the aluminum content increases and a complete hollow shape may not be formed due to fine pores generated on the shell surface. As a result, the strength of the hollow particle decreases, resulting in high-density hollow particles. It cannot be manufactured, and there is undissolved aluminum in the shell, which may cause the refractive index to rise. If it exceeds 15, not only the aluminum on the shell surface but also the core particles are not completely removed when forming micropores in the shell, causing the refractive index to increase. This increases, and it may be difficult to maintain the hollow shape during the hydrothermal reaction.
  • a is the average particle diameter of hollow aluminosilicate particles
  • b is the average particle diameter of amorphous silica particles.
  • the a/b value is the average particle diameter ratio of hollow aluminosilicate particles to amorphous silica particles. If the a/b value is less than 3, the refractive index increases due to the large diameter amorphous silica particles, and the hollow aluminosilicate If the amorphous silica particles do not sufficiently fill the space between the particles, the flatness of the coating film may be reduced, and if it is greater than 15, the flatness of the coating film may be reduced due to the large diameter hollow aluminosilicate particles.
  • the cured film formed from the resin composition for an antireflection film may have a refractive index of 1.20 to 1.35 at 550 nm.
  • the C 1 -C 4 alkoxy group used in this specification refers to a straight-chain or branched alkoxy group consisting of 1 to 4 carbon atoms, and includes, but is not limited to, methoxy, ethoxy, n-propanoxy, etc.
  • R 7 is a hydrogen atom or a C 1 -C 20 alkyl group
  • n is an integer from 1 to 3.
  • the amorphous silica particles may be included in an amount of 20 to 70% by weight, preferably 30 to 50% by weight, based on 100% by weight of the total solid content in the resin composition for an antireflection coating. If the amorphous silica particles are included in an amount of less than 20% by weight, the surface roughness of the paint film may increase due to insufficient filling between the hollow aluminosilicate particles in the paint film, and if the amorphous silica particles are included in an amount exceeding 70% by weight. When this happens, the content of hollow aluminosilicate particles is relatively reduced, making it difficult to lower the refractive index.
  • the first binder resin may have a thermosetting functional group as described above.
  • L 1 to L 4 each independently do not exist or are a C 1 -C 10 alkylene group or a C 1 -C 10 oxyalkylene group.
  • the first binder resin may further have a hydrolyzable silyl group in order to further improve the high temperature and high humidity resistance of the formed coating film and the resistance to developer and stripper through bonding with hollow aluminosilicate particles.
  • the first binder resin may have a thermosetting functional group and a hydrolyzable silyl group.
  • the first binder resin contains one or more of the repeating units represented by the following formulas 1 to 4, and one or more of the repeating units represented by the following formula 5. May contain repeat units.
  • R 1 to R 5 are each independently a hydrogen atom or a methyl group
  • R 6 is a hydroxy group, an alkoxy group of C 1 -C 4 or a halogen
  • R 7 is a hydrogen atom or a C 1 -C 20 alkyl group
  • n is an integer from 1 to 3.
  • the first binder resin improves the degree of curing of the coating film by smoothly bonding with the epoxy group, and improves the high temperature and high humidity resistance of the formed coating film and resistance to developer and stripper, a repeating unit represented by the following formula (6) It may further include.
  • R 8 is a hydrogen atom or a methyl group
  • the first binder resin has a molar ratio of one or more of the repeating units represented by Formulas 1 to 4 and the repeating unit represented by Formula 5 of 10:90 to 90:10, preferably It may be 20:80 to 80:20, more preferably 30:70 to 70:30, and even more preferably 40:60 to 60:40.
  • the formed coating film has excellent high temperature and high humidity resistance and resistance to developers and strippers.
  • the first binder resin may have a polystyrene conversion weight average molecular weight (hereinafter simply referred to as 'weight average molecular weight') measured by gel permeation chromatography (GPC; using tetrahydrofuran as an elution solvent) of 1,000 to 30,000. If the weight average molecular weight of the second binder resin is within the above range, the hardness of the coating film can be improved and reliability such as solvent resistance can be improved.
  • 'weight average molecular weight' measured by gel permeation chromatography
  • leveling agent commercially available surfactants can be used, for example, silicone-based, fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric, etc. surfactants, and these can be used alone. Two or more types may be used in combination.
  • the leveling agent may be included in an amount of 0.0001 to 0.01% by weight based on 100% by weight of the total resin composition for an anti-reflection film. If the content of the leveling agent is within the above range, it is preferable because the film forming property of the resin composition for an anti-reflective film is excellent and the flatness of the coating film formed therefrom becomes good.
  • the curing agent is used to improve deep hardening and mechanical strength, and specific examples of the curing agent include epoxy compounds, polyfunctional isocyanate compounds, melamine compounds, and oxetane compounds.
  • oxetane compound in the curing agent examples include carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, and cyclohexanedicarboxylic acid bisoxetane.
  • slip improvement agent examples include commercially available BYK-333 (BYK).
  • silane-based compounds are preferable, and specifically, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, N-(2-aminoethyl)- 3-Aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-gly Sidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxy Propyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-iso
  • anti-agglomeration agent examples include sodium polyacrylate.
  • the anti-reflection film can be manufactured by applying the above-described anti-reflection film resin composition on a substrate and then applying heat.
  • the resin composition for an anti-reflective film is applied on a substrate and then heated and dried to remove volatile components such as solvents to obtain a smooth coating film.
  • the application method may be, for example, spin coating, flexible coating, roll coating, slit and spin coating, or slit coating.
  • heating temperature is usually 70 to 200°C, preferably 80 to 130°C.
  • a heating process (post-bake) is performed again to form a hardening network.
  • the heating temperature is usually about 70 to 230°C.
  • Heating methods include a hot plate, clean oven, or infrared heater. However, the present invention does not limit the heating method.
  • the solid-state imaging device includes a support including a semiconductor device or a photoelectric conversion device and a micro lens, and the anti-reflection film may be formed on the micro lens.
  • a binder resin solution was obtained by performing the same process as Synthesis Example 1, except that 168.1 g (1 mol) of the mixture of Formula 1-1 and Formula 3-1 (molar ratio 50:50) was used as a monomer.
  • the weight average molecular weight of the obtained binder resin (C-5) was 8,700 and the molecular weight distribution was 1.86.
  • Synthesis Example 6 Synthesis of binder resin (C-6) having a thermosetting functional group and a hydrolyzable silyl group
  • Synthesis Example 8 Synthesis of binder resin (C-8) having thermosetting functional group and hydrolyzable silyl group
  • a core template for the hollow mold was prepared by adding 0.172 g of polyacrylic acid, 0.086 g of polystyrene sulfonic acid, and 3 ml of ammonium hydroxide to a 1L three-necked round flask, and then adding 60 ml of ethanol. While stirring the solution, 8 ml of 3% aluminum isopropoxide and 60 ml of ethanol containing tetra ethoxysilane were added using a syringe pump to obtain spherical particles including a core. These particles were reacted with 5% sodium hydroxide, washed with distilled water and alcohol, and dried to prepare hollow aluminosilicate particles.
  • a dispersion of hollow aluminosilicate particles was obtained in the same manner as Preparation Example 1-1, except that 10 ml of 3% aluminum isopropoxide was used.
  • the average particle diameter was 88 nm, and the Si/Al molar ratio was 10.
  • a dispersion of hollow aluminosilicate particles was obtained in the same manner as Preparation Example 1-1, except that 12 ml of 3% aluminum isopropoxide was used.
  • the average particle diameter was 88 nm, and the Si/Al molar ratio was 8.
  • a dispersion of hollow aluminosilicate particles was obtained in the same manner as Preparation Example 1-1, except that 6 ml of 3% aluminum isopropoxide was used.
  • the average particle diameter was 84 nm, and the Si/Al molar ratio was 16.
  • a hollow silica particle dispersion was obtained in the same manner as Preparation Example 1-1, except that the addition of 3% aluminum isopropoxide was omitted.
  • the average particle diameter was 88 nm.
  • the hollow aluminosilicate particles (A-1) prepared in Preparation Example 1-1 were dried in a dry oven at 120°C for more than 3 hours and then cooled to room temperature in a desiccator to remove adsorbed moisture. used.
  • the solvent make 300 ml of ethanol and deionized water at a ratio of 80:20 (v/v%) at room temperature and pressure, then adjust the pH to 3 to 5 using acetic acid and stir to about 30% at 300 rpm using a magnetic stirrer. It was stirred for a minute.
  • Preparation Example 2 except that the hollow aluminosilicate particles (A-2) prepared in Preparation Example 1-2 were used instead of the hollow aluminosilicate particles (A-1) prepared in Preparation Example 1-1.
  • Surface-modified hollow aluminosilicate particles (E-2) were prepared in the same manner as -1.
  • Preparation Example 2 except that the hollow aluminosilicate particles (A-3) prepared in Preparation Example 1-3 were used instead of the hollow aluminosilicate particles (A-1) prepared in Preparation Example 1-1.
  • Surface-modified hollow aluminosilicate particles (E-3) were prepared in the same manner as -1.
  • Preparation Example 2 except that the hollow aluminosilicate particles (A-4) prepared in Preparation Example 1-4 were used instead of the hollow aluminosilicate particles (A-1) prepared in Preparation Example 1-1.
  • Surface-modified hollow aluminosilicate particles (E-4) were prepared in the same manner as -1.
  • Preparation Example 2-1 except that the hollow silica particles (A-6) prepared in Preparation Example 1-6 were used instead of the hollow aluminosilicate particles (A-1) prepared in Preparation Example 1-1.
  • Surface-modified hollow silica particles (E-6) were prepared in the same manner as above.
  • Aluminosilicate particles (E-7) were prepared.
  • Aluminosilicate particles (E-8) were prepared.
  • Aluminosilicate particles (E-10) were prepared.
  • a resin composition for an anti-reflective film was prepared by mixing each component in the composition shown in Tables 1 to 3 below (% by weight).
  • Example 7 Example 8 Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 Example 15 Example 16 Surface-modified hollow aluminosilicate particles (E) E-1 1.0 2.0 E-2 2.0 3.0 3.5 E-3 2.0 E-4 E-5 E-6 E-7 1.0 E-8 1.0 E-9 1.0 1.0 E-10 Amorphous silica particles (B) B-1 3.2 2.4 2.4 1.6 1.2 3.2 3.2 3.2 3.2 B-2 2.4 B-3 B-4 Binder Resin (C) C-6 0.8 0.3 0.8 0.8 0.8 C-7 0.6 C-8 0.6 0.6 0.4 C-9 0.8 C-10 Solvent (D) D-1 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0 95.0
  • A-1 to A-5 hollow aluminosilicate particles prepared in Preparation Examples 1-1 to 1-5, respectively
  • A-6 Hollow silica particles prepared in Preparation Example 1-6
  • A-7 HSHI-C100 (average particle diameter 182 nm, KC Tec)
  • E-1 to E-5 Surface-modified hollow aluminosilicate particles of Preparation Examples 2-1 to 2-5, respectively.
  • E-7 to E-10 Surface-modified hollow aluminosilicate particles of Preparation Examples 2-7 to 2-10, respectively.
  • An anti-reflection film was manufactured as follows using the resin composition for an anti-reflection film prepared in the above Examples and Comparative Examples, and the physical properties of the anti-reflection film were evaluated in the following manner, and the results are shown in Tables 4 to 6 below. In addition, a/b values were calculated and shown in Tables 4 to 6. At this time, a is the average particle diameter of the hollow aluminosilicate particles, and b is the average particle diameter of the amorphous silica particles.
  • the anti-reflection film resin compositions prepared in the above examples and comparative examples were spin-coated on a 4-inch silicon wafer (manufactured by SK Siltron), and then pre-coated at 100°C for 60 seconds using a hot plate. Baked. The pre-baked substrate was cooled to room temperature and then post-baked for 300 seconds in an oven at 200°C. The thickness of the cured film was 100 nm.
  • n( ⁇ ) is the refractive index at ⁇ wavelength
  • ⁇ is in the range of 300 nm to 1800 nm
  • A, B, and C are Cauchy parameters.
  • a cured film substrate was manufactured in the same manner as the above manufacturing method, except that the thickness of the cured film was formed to be 500 nm.
  • the Ra value of the prepared cured film substrate was measured using an Atomic Force Microscope (AFM) Nanoscope (Bluecar AXS), and the flatness of the coating film was evaluated according to the following evaluation criteria.
  • AFM Atomic Force Microscope
  • Bluetooth AXS Bluecar AXS
  • ⁇ : Ra value is less than 4nm
  • Ra value is 4nm or more and less than 6nm
  • Ra value is 6nm or more and less than 9nm
  • ⁇ Ra value is 9nm or more
  • the refractive index was measured before and after storage for 500 hours in a thermohygrostat PR-1J (ESPEC) at a temperature of 85°C/humidity of 85%, and the change in refractive index was calculated using Equation 2 below and evaluated according to the following evaluation criteria. Accordingly, the moisture permeability at high temperature and high humidity was evaluated.
  • ESPEC thermohygrostat PR-1J
  • ⁇ 1% or more but less than 5%
  • the refractive index was measured before and after 5 minutes immersion in 2.38% tetramethylammonium hydroxide (TMAH) (developer) and methylpyrrolidone (stripper), respectively, and the refractive index change was calculated using Equation 3 below. Therefore, according to the evaluation criteria below, the developer and stripper Moisture permeability was evaluated.
  • TMAH tetramethylammonium hydroxide
  • stripper methylpyrrolidone
  • Refractive index change [(Refractive index after immersion - Refractive index before immersion)/Refractive index before immersion] ⁇ 100

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne : une composition de résine pour un film antireflet, la composition de résine comprenant des particules creuses d'aluminosilicate, des particules de silice amorphe, une première résine liante ayant un groupe fonctionnel thermodurcissable, et un solvant, les particules creuses d'aluminosilicate ayant un rapport molaire Si/Al de 7 à 15 ; un film antireflet formé à partir de celle-ci ; et un dispositif d'imagerie à semi-conducteurs comprenant le film antireflet. Lorsque la composition de résine pour un film antireflet selon la présente invention est utilisée pour former un film de revêtement, la formation de fissures est supprimée, le film de revêtement a une excellente planéité, une absorption d'humidité à haute température et à humidité élevée est empêchée, et la pénétration par une solution de révélateur et une solution de décapage peut être empêchée.
PCT/KR2023/021580 2023-01-02 2023-12-26 Composition de résine pour film antireflet, film antireflet et dispositif d'imagerie à semi-conducteurs WO2024147537A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2023-0000400 2023-01-02
KR20230000400 2023-01-02
KR1020230137665A KR20240108782A (ko) 2023-01-02 2023-10-16 반사방지막용 수지 조성물, 반사방지막 및 고체 촬상 소자
KR10-2023-0137665 2023-10-16

Publications (1)

Publication Number Publication Date
WO2024147537A1 true WO2024147537A1 (fr) 2024-07-11

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20070048727A (ko) * 2004-08-12 2007-05-09 후지필름 가부시키가이샤 반사방지 필름, 편광판 및 이를 이용한 화상 표시 장치
JP2008116522A (ja) * 2006-11-01 2008-05-22 Jsr Corp マイクロレンズ用反射防止膜形成用硬化性樹脂組成物及びマイクロレンズ用反射防止膜
KR101659709B1 (ko) * 2016-05-18 2016-09-26 주식회사 나노신소재 중공형 알루미노실리케이트 입자 및 이의 제조방법
KR20170012380A (ko) * 2015-01-08 2017-02-02 세키스이가세이힝코교가부시키가이샤 중공 입자, 그 제조 방법, 그 용도 및 마이크로 캡슐 입자의 제조 방법
KR20170098166A (ko) * 2016-02-19 2017-08-29 주식회사 엘지화학 저굴절층 형성용 광경화성 코팅 조성물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20070048727A (ko) * 2004-08-12 2007-05-09 후지필름 가부시키가이샤 반사방지 필름, 편광판 및 이를 이용한 화상 표시 장치
JP2008116522A (ja) * 2006-11-01 2008-05-22 Jsr Corp マイクロレンズ用反射防止膜形成用硬化性樹脂組成物及びマイクロレンズ用反射防止膜
KR20170012380A (ko) * 2015-01-08 2017-02-02 세키스이가세이힝코교가부시키가이샤 중공 입자, 그 제조 방법, 그 용도 및 마이크로 캡슐 입자의 제조 방법
KR20170098166A (ko) * 2016-02-19 2017-08-29 주식회사 엘지화학 저굴절층 형성용 광경화성 코팅 조성물
KR101659709B1 (ko) * 2016-05-18 2016-09-26 주식회사 나노신소재 중공형 알루미노실리케이트 입자 및 이의 제조방법

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