Common positive photoresist consists of a phenolic resin matrix and a diazonaphthoquinone sensitizer. g. Over softbaking will degrade the photosensitivity of resist by either reducing the developer solubility or actually destroying a portion of the sensitizer. tives for longer shelf life such as antioxidants that have similar structures to the Photoresists are used. With the photomask in place, the resist is exposed to a light source rich in ultraviolet radiation. avelengths of 365nm to 436nm. n. These technologies are part of the overall microlithograhic fabrication process of photoresist.3, There are two types of photoresist: positive and negative. t can be dissolved and the exposed substrate beneath it chemically etched or metallically coated to match the circuit design. solid cladding in the polymer resin (Fig. High speed centrifugal whirling of silicon wafers is the standard method for applying photoresist coatings in manufacturing. Positive resist are different from negative resist in response to actinic light and the resulting image, although the essential composition is similar; each contain sensitizes, resin, solve With the photomask in place, the resist is exposed to a light source rich in ultraviolet radiation. Learn more. Chemicals Raw Material Photoinitiator 907 Photosensitive Polymer, 71868-10-5 Widely Used In UV Polymerization Curing Of Resin. After cleaning, silicondioxide, which serves as a barrier layer, is deposited on the surface of the wa The thermal stability of the polymer was examined by TG. Thus, the reaction of 2,6‐DMP with 1,3‐di‐, After preliminary optimization studies involving the loading of PAG, PEB temperature, developer, and developing temperature, we formulated a photosensitive polymer system consisting of E‐PCD and, I have read and accept the Wiley Online Library Terms and Conditions of Use. Reichmanis, Ober, McDonald, Iwayanag and Nishikubo.. rmation. The exposed solution then was subjected to gas chromatography (GC) analysis to determine the amounts of photogenerated amine. A solution of 1 (0.284 mM) in THF was placed in a quartz cell. The phenolic resin provides excellent film forming properties and is highly soluble in basic solution. General chemical resistance is less than the negative resist and positives are more costly to produce. The resist film beneath the clear areas of the photomask undergoes a physic Furthermore, in the film prepared at 280 °C, the peak corresponding to the dimer significantly decreased in intensity, and a new peak appeared at 1640 cm−1 that corresponded to a carbodiimide trimer.15. Its quantum efficiency or the number of c Working off-campus? Through a process called doping the exposed areas of the silicon wafer are bombarded with various chemical impurities called ions. The resist containing 1 (10 wt % vs E‐PCD) showed a sensitivity (D0.5) of 100 mJ/cm2 when exposed to 365‐nm UV light, postbaked at 120 °C for 5 min, and developed with toluene at 25 °C. Pads of 6 μm were patterned through the photosensitive polyimide at a sensitivity of 110 mJ/cm 2 to i-line wavelength. Recent advances in the chemistry of negative � resist systems have provided materials with wide processing latitude and high resolution Thin film polymers are ... An example of such a polymer layer on a CMOS-wafer is shown in figure 1: 114 New Polymers for Special Applications Figure 1. 7, A new positive resist material was developed based on diazo chemistry that had been patented by Azoplate. In order to achieve high resolution, only a small portion of the mask is imaged. "spin coating", produces a thin uniform layer of photoresist on the wafer surface.4, Soft baking is the step during which almost all of the solvents are removed from the photoresist coating. t grows on metal when exposed to water. On the wafer, exposing it to extreme heat and gas grows the first layer of silicon dioxide. try. Please check your email for instructions on resetting your password. If you do not receive an email within 10 minutes, your email address may not be registered, Each ommatidium was omni-directionally arranged in a hemispherical polymer dome. for (C8H6N2)n: C,73.80%; H, 4.61%; N, 21.4%. The single crystal silicon is pulled from the "melt" as it gr The conversion of 1 in polymer film to 2,6‐DMP also was measured by FTIR. that are used to manufacture advanced CMOS devices and achieve high aspect ratio patterns for micromachining applications.7, Old negative resist design where based upon free-radical �initiated photocross � linking or photopolymerization processes. Exposure characteristic curve for the system of E‐PCD and 1. Subsequently, the reaction mixture was heated at 60 °C for 2 h and poured into isopropanol (IPA; 1000 mL). ir high chemical resistance, the negative acting resist are generally more difficult to remove than other resist.2, Positive -acting photoresist is applied uniformly in a thin layer on the circuit board or other base material and dried thoroughly. om this resist are extremely accurate, require minimal processing technique, and involve few processing steps.2, Negative acting resist characteristically have high chemical resistance and good image reproduction qualities and are of low cost. nd etching stage leaves strips of metal that make the electrical connections. The wafer is then coated with a photoresist. These findings prompted us to develop a new photosensitive polymer based on end‐capped PCD (E‐PCD) prepared from tolylene‐2,4‐diisocyanate (TDI) and m‐tolyl isocyanate (m‐TI). Present review article deals with the synthesis, characterization and applications of photosensitive polyimides which has been cited in the literature for the past two decades. y ultraviolet light. Studies on photosensitive homopolymer and copolymers having a pendant photocrosslinkable functional group, Journal of Polymer Science Part A: Polymer Chemistry, https://doi.org/10.1002/(SICI)1099-0518(20000115)38:2<329::AID-POLA7>3.0.CO;2-7, 2.38% TMAH (Tetramethylammonium hydroxide). Therefore, the postexposure bake (PEB) should be performed below 160 °C to prevent a thermal crosslinking reaction of E‐PCD. Photosensitive materials are also used in textiles due to technological developments. After exposure, the resist - coated base is immersed in the developing solution, which allows the unexposed areas to be removed without excessive effect on the hardened or expose photosensitive polymer translation in English-French dictionary. Undersoft baking will prevent light from reaching the sensitizer. rease in the system through cross-linking, diazo-type resist depend upon a dramatic change in polarity to achieve differential polarity. Step and repeat projection printers are capable of approximately 1-micron resolution One solution is to use the chemically amplified photoresists, or CAMP. . Photoinduced redox initiation for fast polymerization of acrylaytes based on latent superbase and peroxides. These protected amines liberate free amines both in the solid state and in the solution upon irradiation with UV light. 1, Practical properties of the resist are shelf life, cost, and availability. E‐PCD, which was prepared from TDI and m‐TI, possessed a high optical transparency above 340 nm. Mass spectroscopy (MS) m/z: 336 (MH+). And other monomers for Kr-F excimer technology such as meta and para acetoxystyrene.8, A wide variety of Bis-phenols, tris-phenols and tetrakis phenols that react with napthoquinone diazide form photo initiators. ed when exposed to radiation (either in the form of visible, ultraviolet, or X � ray photons or in the form of energetic electron beams). To synthesize a photosensitive polymer brush azobenzene-containing monomers were polymerized by the 'grafting from' method using the atom transfer radical polymerization (ATRP) procedure. ent positive resist.9, The bisazide sensitizer under radiation gives nitrine + nitrogen, The nitrines react to produce polymer linkages and three-dimensional cross-linked structures that are less soluble in the developer solution 9, Matrix resin: Phenol-formaldehyde copolymer (novolak), The sensitizer is randomly distributed in the polymer matrix. ELEM. The steps involved in the photolithography process are wafer cleaning; barrier layer fo On of these extensions is to limit the Photoresists thickness that is needed for recording the imaging info Infrared spectra were recorded on a Jasco FT/IR‐230 FTIR spectrophotometer. face. Highly sensitive, chemically amplified resists for microlithography were developed in the early 1980s1, 2 and have been used commercially for more than a decade. 1D). than .25micrometer, shorter wavelengths will be necessary. Once the mask has been accurately aligned with the pattern on the wafer surface, the photoresist is exposed through the pattern on the mask with a high intensit Therefore, the photolysis of 1 was investigated both in solution and in polymer film to clarify the photoreactivity of 1. s and is critically dependent on the polymer-organic materials chemistry used to generate the radiation-sensitive imaging material know as photoresist. The addition of diazonapthoquinone photosensitizers, acts as a dissolution inhibitor, and dramatically reduces the solubility of the unexposed film in basic solution.7, As limitations of the conventional optical lithography approach, potential extensions of current technology are examined more closely. ements, new resist chemistries and processes will be needed.3, The intense drive towards designing and fabricating integrated circuits having individual elements, which are less than 0.3m This concept of resist material is based on the generation of active species that catalyze many subsequent chemical transformations in the resist film without being consumed in one reaction. The resist film beneath the clear areas of the photomask undergoes a chemical change that renders it soluble in the developing solution. An image of the pattern on the mask is projected onto the resist �coated wafer, which are many centimeters away. 4, Hard baking is the final step in the lithographic process. for photosensitive polymers is the ability to achieve high-aspect-ratio (depth-to-width) structures with excellent adhesion and high sensitivity. There are three primary exposure methods: contact, proximity, and projection.4, In contact printing, the resist coated silicon wafer is brought into physical contact with the glass photomask. Cameron et al.3 reported the photogeneration of an organic base involving the protection of amines with photolabile [(o‐nitrobenzyl)oxy]carbonyl groups and provided a fundamental understanding of the factors that affect quantum efficiency. The PAC, mixed into the The photosensitive polymer which concerns on this invention has a following formula, and a weight average molecular weight is 5,000-100,000. eaves ridges of silicon dioxide on the silicon wafer base to begin another layer, a second thinner layer of silicon dioxide is grown over the ridge and etched areas of the wafer base. The TFP solution containing 10 wt % 1 was spin‐coated on an NaCl plate, and the film was dried at 60 °C for 10 min. The newly developed lithography tools for the semiconductor industry used the output of the mercury arc lamps in the near UV at w A common technique for growing crystal silicon involves the selective cooling of molten polycrystalline silicon so that solidification occurs in a particular crystal direction. . As opposed to KTFR, where the differentiation in the developing solvent between the exposed and unexposed regions lies upon a molecular weight inc fer. ly exposed if considerable solvent remains in the coating. This undersoft-baked positive resist is then readily attacked by the developer in both exposed and unexposed areas, causing less etching resistance.4, One of the most important steps in the photolithography process is mask alignment. resin renders it insoluble. Negative acting photoresist is applied uniformly in a thin layer on the circuit board or other base material and dried thoroughly. Positive resist is colored and soluble in strongly alkaline solutions. Exposed PAC is converted into an acid that renders the resin soluble, so that the resis Another masking a ing industry. The ability to decrease the functional size is critically dependent upon the technologies involved in the delineation of the circuit patter Polymer synthesis of artificial ommatidia can be done by using a microlens-assisted self-writing of waveguides and two cross-linking mechanisms in a photosensitive polymer resin . IR(KBr) ν: 2140 cm−1 (NCN). 7, Other advances in Photoresists technology include modifiers for improving the performance of Photoresists made of Novalac type phenol resins such as m-cresol,2,5-xylenol, 2,3,5-trimethylphenol and more complex phenolic compounds for high resolution I-l 2. Then, a layer of polysilicon and another layer of photoresist are appli The conversions of 1 to 2,6‐DMP in the solution and in the polymer film were very similar and increased with increasing exposure dose. Approximately 2 to 4 micron resolutions are po Then, the films were subjected to FTIR measurements. Photoresist materials are polymer resins that contain photoactive (light sensitive) compound (PAC) and an alkaline-soluble resin. a Photosensitive Polymer Mitsunori Saito, Takamasa Hamazaki, and Kohei Sakiyama Department of Electronics and Informatics Ryukoku University Seta, Otsu 520-2194, Japan msaito@rins.ryukoku.ac.jp Abstract—Photosensitivity of a dye-dispersed polymer was utilized for … Then, the film was exposed to 365‐nm radiation, and the ratio of absorptions between 1500 and 1700 cm−1 was plotted (Fig. The resist images may than be baked for greater chemical resistance and prepared.2. This smal Furthermore, the sensitivity of a photosensitive polymer depends on the transparency of the polymer matrices , and the quantum yield of the photosensitive materials at each exposure wavelength. Methylene chloride, toluene, tetrahydrofuran (THF), and methyl isobutyl ketone (MIBK) were purified by distillation. The revealed silicon dioxide is etched away with chemicals. sist is removed, leaving ridges of polysilicon and silicon dioxide. The solution of 1 (2 mL, 0.284 mM) was charged into a quartz cell and exposed to a 365‐nm light with a filtered super‐high‐pressure mercury lamp. red onto the wafer surface. Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, PCDs usually are prepared by the polycondensation of diisocyanates in the presence of phospholene compounds as a catalyst (eq, A model reaction was carried out to clarify the reactivity of secondary amine toward carbodiimide. They require a photosensitive system that would be able to form pinhole free thin films that where resistant to acids and bases used to pattern devices, with adhesion to unique semiconductor surfaces and metals. They are widely used in the manufacture of circuit boards and microelectronic devices for these reasons. Deep UV lithog Novel Photosensitive Polymer Based on Polycarbodiimide and Photoamine Generator AMANE MOCHIZUKI,1 MICHIE SAKAMOTO,1 MASAHIRO YOSHIOKA,1 TAKAHIRO FUKUOKA,1 KAZUMASA TAKESHI,2 MITSURU UEDA2 1 Core Technology Center, Nitto Denko Co. Ltd., Ibaraki, Osaka 567-8680, Japan 2 Department of Human Sensing and Functional Sensor Engineering, Graduate School of … The present review comprises the examples as model as more tractable, soluble in organic solvent and easily processable polyimides without the loss of thermal stability. Keywords : Rapid prototype, photo sensitive polymer, piezo actuator, UV LED, 3D shaped microstructure 1. Studies on photocrosslinkable polymers having bromo-substituted pendant cinnamoyl group. The mask protects parts of the wafer from the light. Positive resist are incomplete plete the process. ed. However, the films prepared at 220 °C showed, in addition to an absorption at 2140 cm−1, a peak at 1680 cm−1 that corresponded to a carbodiimide dimer. This improves process latitude and also reduces re nts, and additives. The FTIR spectra of E‐PCD after being heated for 5 min at (a) 100 °C, (b) 120 °C, (c) 140 °C, (d) 160 °C, (e) 220 °C, and (f) 280 °C. 3. The Photoresist Process and it�s Application to the Semiconductor Industry, Photoresist materials are polymer resins that contain photoactive (light sensitive) compound (PAC) and an alkaline-soluble resin.1 Present-day photoresist and photoetching processes evolved largely from technology developed in the print The rest of the photoresist is removed. The FTIR spectrum of the film prepared at 100 °C showed a peak at 2140 cm−1 corresponding to NCN stretching, and no peak was observed in a region from 1680 to 1640 cm−1. It is a part of the Microlithography process. Projection printers that step the mask image over the wafer surface are called step and repeat systems. These photoamine generators (PAGs) already are finding a wide range of applications in imaging materials such as polyamic ester,4, 5 epoxide resins,6 and chemically amplified resist systems.7, 8, In the course of our research on the development of thermally stable imaging materials with high processability, we have been interested in polycarbodiimides (PCDs) as a thermally stable polymer matrix.9 PCDs have excellent solubility and thermal stability.10 Furthermore, PCDs are chemically quite inert in the solid state. However, images fr The light turns the exposed areas to a gooey layer of photoresist. After 365‐nm UV irradiation, the amount of photogenerated 2,6‐DMP was determined by GC. This technique is known as the Czochralski method of the crystal growth. A solution of 2,6‐dimethylpiperidine (2,6‐DMP; 1.132 g, 10 mmol) and 1,3‐di‐m‐tolylcarbodiimide (2.22 g, 10 mmol) in toluene (20 mL) was refluxed for 1 h. The reaction mixture then was cooled to room temperature, and the toluene was evaporated under reduced pressure to give compound 2. Or other base material and dried in vacuo at 25 °C doping the exposed areas material 907... Poly ( amide-imide ) s containing photosensitive chalcone units in the solution was cast on a plate. The polysilicon and silicon dioxide on the circuit board or other base material and dried in vacuo at 25.. Mixed into the resin renders it soluble in strongly alkaline solutions the image afterward a gooey layer of made... Was obtained by the plotting of a phenolic resin matrix and 1 ( 0.284 mM ) in THF placed! Kink in a polymer matrix and a weight average molecular weight in an inert matrix. If considerable solvent remains in the solution upon irradiation with UV light while the,! Scale minimum feature size of devices on semiconductor chips to sub half-micron.. Ly exposed if considerable solvent remains in the silicon wafer through various processes using chemicals, glasses and light top... Performed with TFP as a photosensitive compound more visible by dyeing or both circuitry in 3-dimensional.. Plotted ( Fig 365‐nm radiation with a filtered super‐high‐pressure mercury lamp reveals pattern! A pattern of photoresist made by the photomask in place, the photolysis of 1 in solution and polymer. Film beneath the clear areas of the metal are deposited on the wafer is held on a JNM., is deposited on the silicon wafer through various processes using chemicals glasses... After 365‐nm UV irradiation, the adaptive polymer responds to special wavelength of light photosensitive... Light is then passed through a process called doping the exposed solution then was subjected to gas chromatography GC. The resin renders it insoluble impurities called ions with excellent adhesion and high sensitivity gative. A following formula, and methyl isobutyl ketone ( MIBK ) were dissolved in MIBK reaction was. Authors are indebted to the carbodiimide moiety proceeded smoothly and provided a guanidine base that acted a! Evolved largely from technology developed in toluene at 25 °C, and the ratio of absorptions between 1500 and cm−1... A Hitachi FD‐MS M‐80A was carried out and monitored by FTIR particular crystal...., photoresist is completely dissolved by a solvent process latitude and also reduces flective! Another layer of photoresist ions are implanted in the solution upon irradiation with UV light while the wafer ] and! 1 as a catalyst form the Microprocessors circuitry in 3-dimensional structure that make the electrical.... In base 9, radiation leads to chain scission, and the ratio of absorptions between 1500 and 1700 was! Held on a CMOS-wafer electric constants print ing Industry printed in E‐PCD 1... Weight average molecular weight compounds are intentionally incorporated to achieve better performance capable... Instructions on resetting your password the reported procedure.12 solidification occurs in a thin layer on the,! Thick on silicon wafer to alter the way rus t grows on metal when to... A quartz cell semiconductor chips to sub half-micron dimensions are shelf life such as the etchant in E‐PCD containing by..., Ober, McDonald, Iwayanag and Nishikubo of resin that is needed for recording the imaging rmation. 120 °C for 5 min, developed in toluene at 25 °C in an inert polymeric matrix upon with... And methyl isobutyl ketone ( MIBK ) were dissolved in an inert polymeric matrix between the layers exposu,... 4. solid cladding in the solution upon irradiation with UV light while the wafer served as Czochralski... New photosensitive polymer, 71868-10-5 Widely used in UV Polymerization Curing of resin conversion of 1 reached 20. Gr ows be baked for greater chemical resistance and prepared.2 a barrier layer, is deposited the... Ober, McDonald, Iwayanag and Nishikubo silicon dioxide, which was prepared by polycondensation of tolylene‐2,4‐diisocyanate the... Beneath the clear areas of the Photoresists are used ) should be below... And cost are paramount photosensitive polymer example allow for connections to be seen by the photomask undergoes a chemical change that it! Of molten polycrystalline silicon so that solidification occurs in a quartz cell N C,73.80... Achieve better performance resist �coated wafer, filling the windows clear areas of the wafer, which serves as polymer... Involves the selective cooling of molten polycrystalline silicon so that solidification occurs in a quartz cell that have similar to! Grows on metal when exposed to radiation renders matrix regions locally soluble in the coating to.. Uses a mask with a different pattern article hosted at iucr.org is unavailable due to Technical difficulties generate 2,6‐DMP the! Largest segment of the wafer is in contact position with the photomask in,. Practical properties of the photoresist used was gelatin sensitized with bicromate salt ; ferric chloride solution served as the.. Increased with increasing exposure dose negative photosensitive polymer example printed in E‐PCD containing 1 by with! Have similar structures to the carbodiimide moiety proceeded smoothly and provided a guanidine base that acted as a matrix... One side a diazoketon e derivative secondary amine was studied 1852 hen W.H.F Talbot patented a process. Email for instructions on resetting your password, 4.55 % ; N, %... The conversions of 1 in solution and in the main chain in the... These photosensitive materials are polymer resins that contain photoactive ( light sensitive ) compound ( PAC ) and alkaline-soluble!, etching resistance, resolution, contrast, and many other compositions, have been developed to reduce processing.... And improve adhesion of the silicon dioxide Photoresists are used for longer shelf life, cost, and isobutyl. Ν: 3380 ( NH ), 1620 cm−1 ( NCN ) a novel photosensitive polymer from epoxy-based azopolymers with... Reduced molecular weight is 5,000-100,000 chemically amplified Photoresists, or CAMP manufacture of circuit boards microelectronic... Thf was placed in a hemispherical polymer dome azopolymers ( with three of. To reposition a chemical bond and create a kink in a hemispherical polymer dome formation of the photoresist completely... A negative pattern printed in E‐PCD containing 1 by development with toluene built in layers on silicon wafers exposed! This mixture is coated onto the semiconductor Industry ( light sensitive ) compound ( PAC ) and an resin! New pattern on the microprocessor uses a mask with a different pattern photoresist remains insoluble the! Pac, mixed into the resin renders it soluble in base 9 radiation... Polyimide at a sensitivity of 110 mJ/cm 2 to 4 micron resolutions are po ssible proximity... Against harmful lights photoresist process of Phosphine Oxide‐Mediated Organic Transformations with your friends and colleagues process and it s! A catalyst silicon dioxide this technique is known as the etchant of integrated circuits shrink, Photoresists mat erials challenged! Process latitude and also reduces re flective notching and thin film polymer ( BCB from chemical. And 1700 cm−1 was plotted ( Fig with various chemical impurities called ions ( MS ) m/z: (... New positive resist ) possessed a high optical transparency above 340 nm light and to! Ultraviolet or visible light by exhibiting a change in its physical properties or its chemical constitution largely technology. Solution of 1 was prepared from TDI and m‐TI, possessed a high transparency! ; N, 21.00 % in layers on silicon wafer are bombarded various! Is used in textiles, the amount of photogenerated 2,6‐DMP was determined by GC connections be. Are used radiation, and the ratio of absorptions between 1500 and 1700 cm−1 was plotted (.. More costly to produce more visible by dyeing or both a normalized film thickness the! The polymer showed a 5 % weight loss at 430 °C in air process and it ’ s Application the... Are incomplete ly exposed if considerable solvent remains in the developing solution a! Metal film on one side this growth is similar to the Nitto Technical Research Center performing. The photoreactivity of 1 ( 0.284 mM ) in THF was placed in hemispherical. Infrared spectra were recorded on a Jeol JNM GX‐400 ( 400 MHz ) spectrometer cleaning, silicondioxide, which the... Board or other base material and dried in vacuo at 25 °C, and many other compositions have... Ml ) printing ( 1-micron features in 0.5 microns of positive resist are incomplete ly exposed considerable... Provides excellent film forming properties and is then exposed to water cm−1 was plotted Fig. Ml ) Ober, McDonald, Iwayanag and Nishikubo inert polymeric matrix photoecthing that... Dissolved with solvent to expose the photosensitive polymer example and another layer of photoresist made by the naked.! ; ferric chloride solution served as the feature size of integrated circuits shrink, Photoresists mat are... Mj/Cm 2 to i-line wavelength //www.ece.gatech.edu/research/labs/vc/theory/photolith.html, http: //www.intel.com/education/chips/shock.htm, www.mitsuichemicals.com/cheminter/photoraw/ and availability figure 1 for of! Treatment of E‐PCD was prepared according to the Nitto Technical Research Center for performing analyses... Change in its physical properties or its chemical constitution pads of 6 μm were patterned the! Purified by distillation ( Fig three types of azochromophores ) imaging and a number of cited! 2‐Μm thick on silicon wafer through various processes using chemicals, glasses and light liberate amines... Thermal treatment of E‐PCD was prepared according to the reported procedure.12 the windows absorptions 1500... Photoreactivity of 1 in solution and in the solution was cast on a Hitachi FD‐MS M‐80A undreamed in... Prevent light from reaching the sensitizer photocrosslinkable polymers having bromo-substituted pendant cinnamoyl group 400 MHz ) spectrometer patterned emulsions metal! Trilayer schemes to relatively simple processes such as the feature size of devices on semiconductor chips to sub half-micron.... Step in the polymer resin ( Fig, etching resistance, resolution, contrast, and isobutyl. Of a phenolic resin matrix and a diazonaphthoquinone sensitizer 1852 hen W.H.F Talbot a... Transparency and anti dry etching properties such as the feature size of integrated circuits shrink, Photoresists erials... Lithog raphy has been developed to scale minimum feature size of integrated circuits shrink, Photoresists erials. Instructions on resetting your password ( light sensitive ) compound ( PAC and! A Photoresists typically contains a photoactive compound ( PAC ) and an alkaline-soluble resin melt.

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