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  Novel resins and photoresist compositions comprising sameUSPTO Application #: 20080032232Title: Novel resins and photoresist compositions comprising same Abstract: Provided are new resins that comprise carbocyclic aryl units with hetero substitution units and photoresists that contain such resins. Particularly preferred photoresists of the invention comprise a deblocking resin that contains hydroxy naphthyl units and can be effectively imaged with sub-200 nm radiation such as 193 nm radiation. (end of abstract) Agent: S. Matthew Cairns Rohm And Haas Electronic Materials LLC - Marlborough, MA, US Inventors: Young C. Bae, George G. Barclay USPTO Applicaton #: 20080032232 - Class: 430286100 (USPTO) Related Patent Categories: Radiation Imagery Chemistry: Process, Composition, Or Product Thereof, Imaging Affecting Physical Property Of Radiation Sensitive Material, Or Producing Nonplanar Or Printing Surface - Process, Composition, Or Product, Radiation Sensitive Composition Or Product Or Process Of Making, N-vinylidene, Resin Or Prepolymer Containing Ethylenical Unsaturation The Patent Description & Claims data below is from USPTO Patent Application 20080032232. Brief Patent Description - Full Patent Description - Patent Application Claims
BACKGROUND OF THE INVENTION [0001] 1. Field of the Invention [0002] The present invention relates to new resins that comprise carbocyclic aryl units with hetero substitution (particularly hydroxy or thio) and photoresists that contain such resins. Preferred photoresists of the invention comprise a resin that contains hydroxy naphthyl groups. [0003] 2. Background [0004] Photoresists are photosensitive films used for transfer of images to a substrate. A coating layer of a photoresist is formed on a substrate and the photoresist layer is then exposed through a photomask to a source of activating radiation. The photomask has areas that are opaque to activating radiation and other areas that are transparent to activating radiation. Exposure to activating radiation provides a photoinduced chemical transformation of the photoresist coating to thereby transfer the pattern of the photomask to the photoresist-coated substrate. Following exposure, the photoresist is developed to provide a relief image that permits selective processing of a substrate. [0005] A photoresist can be either positive-acting or negative-acting. For most negative-acting photoresists, those coating layer portions that are exposed to activating radiation polymerize or crosslink in a reaction between a photoactive compound and polymerizable reagents of the photoresist composition. Consequently, the exposed coating portions are rendered less soluble in a developer solution than unexposed portions. For a positive-acting photoresist, exposed portions are rendered more soluble in a developer solution while areas not exposed remain comparatively less developer soluble. Photoresist compositions are described in Deforest, Photoresist Materials and Processes, McGraw Hill Book Company, New York, ch. 2, 1975 and by Moreau, Semiconductor Lithography, Principles, Practices and Materials, Plenum Press, New York, ch. 2 and 4. [0006] While currently available photoresists are suitable for many applications, current resists also can exhibit significant shortcomings, particularly in high performance applications such as formation of highly resolved sub-half micron and sub-quarter micron features. [0007] Consequently, interest has increased in photoresists that can be photoimaged with short wavelength radiation, including exposure radiation of less than 200 nm, such as wavelengths of about 193 nm. Use of such short exposure wavelengths can enable formation of smaller features. Accordingly, a photoresist that yields well-resolved images upon 193 nm exposure could enable formation of extremely small (e.g. sub-0.25 .mu.m) features that respond to constant industry demands for smaller dimension circuit patterns, e.g. to provide greater circuit density and enhanced device performance. [0008] Silicon oxynitride (SiON) layers and other inorganics such as Si.sub.3N.sub.4 coatings have been employed in semiconductor device manufacture, for example as an etch stop layer and an inorganic antireflective layer. See, for instance, U.S. Pat. Nos. 6,124,217; 6,153,504; and 6,245,682. SUMMARY OF THE INVENTION [0009] We now provide new resins that contain a repeat unit that comprises a carbocyclic aryl unit substituted with one or more hetero-atom containing groups, particularly a carbocyclic aryl unit substituted with one or more oxygen or sulfur-containing groups. Such resins are particularly useful as a component of a photoresist composition. [0010] We have surprisingly found that incorporation of such substituted carbocyclic aryl units into a polymer can provide significant improvements in lithographic performance of a photoresist containing the polymer. In particular, we have found that use of a resin that contains substituted carbocyclic aryl groups such as hydroxy naphthyl in a photoresist can enable development of a relief image of a significantly enhanced smooth profile (i.e. reduced line edge roughness). See, for instance, the comparative results set forth in the examples which follow. [0011] We also have found that photoresists of the invention can adhere to inorganic surface layers, including SiON layers. See, for instance, the results set forth in Example 6 which follows. We have found that prior photoresists can adhere relatively poorly to such inorganic surface coatings, resulting in reduced resolution of a patterned image. [0012] Preferred substituted carbocyclic aryl units for incorporation into a resin are naphthyl groups as well as other substituted carbocyclic aryl moieties such as hetero-substituted phenyl, anthracenyl, acenaphthyl, phenanthryl, and the like. Generally, hetero-substituted carbocyclic aryl groups having multiple fused rings (e.g. 2 or 3 fused rings, at least one of which is a carbocyclic aryl) are preferred such as hetero-substituted naphthyl, anthracenyl, acenaphthyl, phenanthryl, and the like. [0013] A carbocyclic group may have a variety of hetero-substituents, with oxygen- and sulfur-containing substituents being generally preferred. For instance, preferred hetero-substituted carbocyclic aryl groups of resins of the invention include those aryl groups having one or more hydroxy (--OH), thio (--SH), alcohol (e.g. hydroxyC.sub.1-6alkyl), thioalkyl (e.g. HSC.sub.1-6alkyl), alkanoyl (e.g. C.sub.1-6alkanoyl such as formyl or acyl), alkylsulfide such as C.sub.1-6alkylsulfide, carboxylate (including C.sub.1-12ester), alkyl ether including C.sub.1-8ether, and the like. Preferably, at least one hetero atom of the hetero-containing substituent has a hydrogen substituent (e.g. hydroxy is preferred over alkoxy). It is also preferred that the hetero group has the hetero atom directly linked to the carbocyclic ring (such as a hydroxy or thio ring substituents), or a hetero atom is a substituent of an activated carbon such as a ring substituent of --CH.sub.2OH or --CH.sub.2SH, or other primary hydroxy or thio alkyl. [0014] Preferred resins of the invention comprise repeat units in addition to substituted carbocyclic aryl units, particularly non-aromatic units such as provided by polymerization of an acrylate or an optionally substituted cyclic olefin (particularly carbon alicyclic or heteroalicyclic group) such as a polymerized optionally substituted norbornene. Preferably, for resin used in positive-acting resists, at least one of the resin repeat units contains a photoacid-labile moiety such as a photoacid-labile ester or acetal moiety. Particularly preferred resins are substantially free of any aromatic moieties other than the hydroxy naphthyl groups or other hetero-substituted carbocyclic aryl groups. [0015] Additional preferred polymer units may be provided by polymerization of an anhydride such as maleic anhydride or itaconic anhydride; or lactones such as provided by polymerization of a suitable acrylate e.g. acryloxy-norbornane-butyrolactone and the like. [0016] Photoresists of the invention preferably comprise one or more photoacid generator compounds (PAGs) as a photoactive component. Preferred PAGs for use in resists of the invention include onium salt compounds including iodonium and sulfonium compounds; and non-ionic PAGs such as imidosulfonate compounds, N-sulfonyloxyimide compounds; diazosulfonyl compounds and other sulfone PAGS including .alpha.,.alpha.-methylenedisulfones, disulfonehydrazines and disulfonylamine salts; nitrobenzyl compounds, halogenated particularly fluorinated non-ionic PAGS. [0017] Photoresists of the invention also may contain a blend of resins, where at least one of the resins contains hydroxy naphthyl units or other hetero-substituted carbocyclic aryl groups. Preferably each member of the resin blend contains hydroxy naphthyl units or other hetero-substituted carbocyclic aryl groups. [0018] Photoresists of the invention include both positive-acting and negative-acting compositions. Negative-acting compositions suitably comprise a separate crosslinker component, such as an amine-based material, e.g. a melamine or benzoguanamine resin. [0019] The invention also includes methods for forming relief images, including methods for forming a highly resolved relief image such as a pattern of lines (dense or isolated) where each line has vertical or essentially vertical sidewalls and a line width of about 0.40 microns or less, or even about 0.25, 0.20, 0.15, or 0.10 microns or less. In such methods, preferably a coating layer of a resist of the invention is imaged with short-wavelength radiation, particularly sub-200 nm radiation, especially 193 nm radiation, and higher energy radiation having a wavelength of less than 100 nm, and otherwise high energy radiation such as EUV, electron beam, ion beam or x-ray. The invention further comprises articles of manufacture comprising substrates such as a microelectronic wafer having coated thereon the photoresists and relief images of the invention. The invention also provides methods for manufacturing such articles. Other aspects of the invention are discussed infra. BRIEF DESCRIPTION OF THE DRAWINGS [0020] FIGS. 1 and 2 show oxide etch results of the Examples 3 and 4 which follow. [0021] Examples 3, 4 and 5 show Scanning Electron Micrograph (SEM) of photoresists of Examples 5 and 6 which follow. Continue reading... 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