WO2013134997A1 - 含双酚a骨架结构的分子玻璃光刻胶及其制备方法和应用 - Google Patents
含双酚a骨架结构的分子玻璃光刻胶及其制备方法和应用 Download PDFInfo
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- WO2013134997A1 WO2013134997A1 PCT/CN2012/075707 CN2012075707W WO2013134997A1 WO 2013134997 A1 WO2013134997 A1 WO 2013134997A1 CN 2012075707 W CN2012075707 W CN 2012075707W WO 2013134997 A1 WO2013134997 A1 WO 2013134997A1
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- 0 *c1cc(*)cc(O)c1 Chemical compound *c1cc(*)cc(O)c1 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/92—Systems containing at least three condensed rings with a condensed ring system consisting of at least two mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic system, e.g. cyclophanes
Definitions
- the present invention relates to a series of molecular glass photoresists comprising a bisphenol A framework structure and a process for the preparation of such compounds and their use in lithography, especially in extreme ultraviolet lithography. Background technique
- the photoresist used in 193nm lithography is mainly a polymer system, and 193nm lithography has been difficult to meet as lithography has increased requirements for resolution, sensitivity, and line edge roughness.
- EUV lithography can achieve 32nm and 22nm nodes, even lower technology nodes, by using only 13.5nm light source, which makes EUV lithography will play a very important role in the future lithography field. Important role. Since EUV lithography has different characteristics from other lithography technologies, the corresponding photoresist materials will have more stringent requirements.
- EUV photoresists require low absorbance, high transparency, high etch resistance, high resolution (less than 22nm), high sensitivity, low exposure dose (less than 10mJ/cm 2 ), high environmental stability, low gas production and low Line edge roughness (less than 1. 5nm) and the like. Therefore, the original polymer system cannot meet the requirements of EUV lithography due to its large molecular weight and non-uniformity. The development of such new photoresists is very important.
- Molecular glass is a small molecular organic compound with a high glass transition temperature (TJ). It combines the advantages of a polymer with a small molecule. It has a small molecular weight and is monodispersed, and has an amorphous state. It has high thermal stability. And it has a glass transition process peculiar to polymer compounds, and is an ideal photoresist material. Due to the excellent properties of molecular glass photoresist, it can be used not only in the traditional 248nm and 193nm lithography technologies. It will become the preferred host compound material for next-generation lithography technologies such as EUV lithography, nanoimprint lithography and electron beam lithography.
- TJ glass transition temperature
- the more common molecular glass photoresists are benzene polyphenol type photoresists and calixarene-based photoresists, and through different degrees of protection of their reactive hydroxyl groups (such as tert-butyloxycarbonyl or adamantyl protection), It can be combined with photoacid generators, crosslinkers, photoresist solvents and other additives to obtain positive or negative photoresists with different properties.
- Another object of the present invention is to provide a method for producing the above molecular glass.
- the molecular glass containing the bisphenol A skeleton structure provided by the invention has two types of benzene polyphenol type and calixarene type, and the structural formulas thereof are as follows: (I) and (I I ):
- the alkyl group represents a linear or branched alkyl group having 1 to 8 carbon atoms, for example, a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a t-butyl group or the like.
- the benzene polyphenol type and calixarene type molecular glasses (I) and (II) of the present invention are prepared by modifying a bisphenol A skeleton structure by a Suzuk i coupling reaction, and introducing a polyhydroxy group into the structure of the prepared compound. And with different levels of protection through protecting groups.
- X is independently selected from the group consisting of H, d- 8 alkyl, -COOd- 8 R independent
- R 3 is optionally d- 8 alkyl
- R is selected as d- 8 alkyl
- Z is a halogen (preferably chlorine)
- a cup-type aromatic molecular glass having different degrees of protection that is, a compound of the formula ( ⁇ )
- step (i) or step (1) is preferably carried out in the presence of a carbonic acid clock, preferably using acetone as a solvent, and the reaction temperature is preferably from 50 to 60.
- C the time is preferably 10 ⁇ 15h, wherein the ratio of the general formula (III) tetrabromobisphenol A (or formula (IV)) to the halogen or acid diester (ZY or S0 2 (0-Y) 2 ) A molar ratio of 1:3 is preferred.
- the step (ii) or the step (2) described above is preferably carried out under the catalytic conditions of tetrakis(triphenylphosphine)palladium.
- a base such as a solution of carbonic acid 4
- the solvent is preferably dioxane-water
- the reaction temperature is preferably 90 to 110 ° C
- the time is preferably 12 to 36 h
- the molar ratio of the feed to the phenylboronic acid derivative is preferably 1:6 (or 1:1.5).
- step (iii) or step (3) it is preferred to carry out the dealkylation reaction using boron tribromide or hydrogen bromide, and the solvent used for the reaction is preferably dichloromethane or acetic acid, and the reaction is preferably carried out at room temperature.
- the reaction time is preferably 6 to 24 hours.
- step (iv) or step (4) is preferably carried out at room temperature under the catalysis of 4 or 4-dimethylaminopyridine (DMAP), the reaction time is preferably 2-12 h, and the reaction solvent is preferably tetrahydrofuran or acetone, and the product is preferably Purification by column chromatography on ethyl acetate / petroleum ether over silica gel.
- DMAP 4-dimethylaminopyridine
- the molecular glass (I) or (II) in the present invention wherein the unprotected molecular glass of the hydroxyl group (ie, the fluorenyl hydroxyl group in the structure) can be used as a negative photoresist, and the hydroxy-protected molecular glass can be used as a positive lithography.
- the molecular glass protected by hydroxyl groups can be used as a positive or negative photoresist.
- the present invention further provides a negative photoresist composition
- a negative photoresist composition comprising a hydroxy group unprotected or partially protected molecular glass (I) or (II) which can be used as a negative photoresist, and a photoacid generator, a crosslinking agent , photoresist solvent.
- the above-mentioned molecularly unprotected or partially protected molecular glass (I) or (II) which can be used as a negative photoresist means that at least one of -0 and R in the general formula (I) or (II) is - 0H.
- the negative photoresist composition preferably contains 0.1% to 10% by mass of the general formula (I) or (II), 0.01% to 1% by mass of the crosslinking agent, 0.01% to 1 % (mass ratio) of photoacid generator.
- the present invention further provides a positive photoresist composition
- a positive photoresist composition comprising a hydroxyl-protected or partially protected molecular glass (I) or (II) which can be used as a positive photoresist, and a photoacid generator, a photoresist Solvent.
- the above-mentioned hydroxy-protected or partially protected molecular glass (I) or II) which can be used as a positive photoresist means that at least one of -0- and R in the formula (I) or (II) is -Od — 8- alkyl, - OCOOd— 8
- the positive resist composition preferably contains 1% to 10% by mass of a photoacid generator of the formula (I) or (II) and 0.01% to 1% by mass.
- the photoacid generator includes an ionic or nonionic type such as triphenylsulfonium trifluoromethanesulfonate, bis(4-tert-butylphenyl)iodonium p-toluene hydrochloride, and N-hydroxynaphthoic acid.
- An amine trifluoromethanesulfonate or the like the crosslinking agent includes tetramethylglycoluril, 2,4-dihydroxymethyl-6-methylphenol (2,4-DMMP), and the like;
- Solvents include propylene glycol methyl ether acetate (PGMEA), ethyl lactate, ethylene glycol monomethyl ether, cyclohexanone Wait.
- the above positive or negative photoresist composition may also include other additives such as sensitizers, surfactants, dyes, stabilizers and the like.
- Spin coating is performed to obtain a photoresist coating.
- the molecular glass of the present invention is a stereo-asymmetric amorphous small molecule compound which can be dissolved in an organic solvent commonly used for photoresists. It has a high melting point and a glass transition temperature (melting point higher than 100 °C), which can meet the requirements of lithography, and the film structure does not change during high temperature baking.
- the photoresist composition of the present invention can be prepared to obtain a uniform film in which molecular glass as a matrix component is not precipitated.
- the film prepared from the photoresist composition of the present invention has good resolution, photosensitivity, adhesion, and is easy to store, and the photoresist of the present invention can obtain a lithographic pattern of 5 Onm or less.
- the photoresist prepared by the present invention can be used in modern lithography processes such as 248 nm lithography, 193 nm lithography, extreme ultraviolet (EUV) lithography, nanoimprint lithography (NIL) and electron beam lithography (EBL). Especially suitable for use in extreme ultraviolet (EUV) lithography processes.
- EUV extreme ultraviolet
- NIL nanoimprint lithography
- EBL electron beam lithography
- Fig. 1 is a thermogravimetric analysis chart of the molecular glass (1-1) prepared in Example 4.
- Fig. 2 is a thermogravimetric analysis diagram of the molecular glass (1-2) prepared in Example 7.
- Figure 3-4 is an electron micrograph of a lithographic pattern obtained by using a double grating in Example 12.
- Fig. 5 is an electron micrograph of a lithographic pattern obtained by using four gratings in the embodiment 12.
- Example 1 In order to further illustrate the teachings of the present invention, the following series of specific embodiments are given, but the present invention is not limited by these specific embodiments, and any modifications to the present invention by those skilled in the art will achieve similar results. Modifications are also included in the present invention.
- Example 1
- the reaction system was added to a 10 OmL 2N NaOH solution, the aqueous layer was separated, acidified with 5N hydrochloric acid, and then extracted three times with 100 mL of ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and then filtered.
- the white crystals were 5.36 g, and the yield was 89.8%.
- Figure 3-4 shows an electron micrograph of a lithography pattern obtained by using a double grating. The exposure period is 140 nm, and a photoresist trench of about 30 nm can be obtained.
- Figure 5 shows the An electron micrograph of a lithographic pattern obtained by four gratings. As can be seen from the lithographic pattern shown in the above electron micrograph, the photoresist of the present invention has a good resolution and contrast while having a line edge roughness of 4 ⁇ .
- Negative photoresist formulation design 20mg molecular glass I-2C, 5mg tetramethoxymethyl glycoluril crosslinker, 1mg triphenylsulfonium trifluoromethanesulfonate dissolved in lmL PGMEA to form a negative Photoresist, spin-coated on a hydrophilic and hydrophobic silicon wafer (500 ⁇ 1000rpm, 0 ⁇ 30s; 1000 ⁇ 2000rpm, 0 ⁇ 30s;
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
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Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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JP2014561253A JP5977842B2 (ja) | 2012-03-16 | 2012-05-18 | ビスフェノールa骨格構造含有の分子性ガラスフォトレジスト及びその製造方法並びに応用 |
US14/385,238 US9454076B2 (en) | 2012-03-16 | 2012-05-18 | Molecular glass photoresists containing bisphenol a framework and method for preparing the same and use thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CN201210070735 | 2012-03-16 | ||
CN201210070735.2 | 2012-03-16 |
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WO2013134997A1 true WO2013134997A1 (zh) | 2013-09-19 |
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PCT/CN2012/075707 WO2013134997A1 (zh) | 2012-03-16 | 2012-05-18 | 含双酚a骨架结构的分子玻璃光刻胶及其制备方法和应用 |
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US (1) | US9454076B2 (zh) |
JP (1) | JP5977842B2 (zh) |
CN (1) | CN103304385B (zh) |
WO (1) | WO2013134997A1 (zh) |
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WO2016129679A1 (ja) * | 2015-02-12 | 2016-08-18 | 三菱瓦斯化学株式会社 | 化合物、樹脂、リソグラフィー用下層膜形成材料、リソグラフィー用下層膜形成用組成物、リソグラフィー用下層膜、レジストパターン形成方法、回路パターン形成方法及び化合物又は樹脂の精製方法 |
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US9454076B2 (en) | 2016-09-27 |
CN103304385B (zh) | 2015-04-15 |
JP2015514691A (ja) | 2015-05-21 |
US20150037735A1 (en) | 2015-02-05 |
JP5977842B2 (ja) | 2016-08-24 |
CN103304385A (zh) | 2013-09-18 |
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