技术领域technical field
本发明涉及一种紫外光固化材料，具体地说是一种基于巯基-烯光交联反应的紫外光固化纳米压印材料。The invention relates to an ultraviolet light curing material, in particular to an ultraviolet light curing nano imprint material based on mercapto-ene photocrosslinking reaction.
背景技术Background technique
纳米压印技术作为一种不受光刻极限限制、低成本、高分辨率、高产量的图案制备技术，已经获得了广泛的关注。在信息存储、生物传感器和亚波长光学器件等领域，已成为价格相对较低、性能可靠、具有量产能力的制备技术。As a low-cost, high-resolution, and high-throughput pattern preparation technology that is not limited by lithography limits, nanoimprint technology has gained widespread attention. In the fields of information storage, biosensors and sub-wavelength optical devices, it has become a preparation technology with relatively low price, reliable performance and mass production capacity.
纳米压印材料是纳米压印技术的核心要素之一，尤其是在已逐渐成为压印技术主流的紫外光固化纳米压印技术中，低粘度、高分辨率、高刻蚀选择性的紫外光固化薄膜材料已成为影响压印图案保真度、高深宽比结构制备的关键。目前应用于紫外光固化纳米压印技术中的压印材料主要是丙烯酸酯类光交联聚合物。丙烯酸酯类紫外光预聚物固化速率快，但是在有氧环境下不能固化，且固化后有较大的体积收缩率。Nanoimprint materials are one of the core elements of nanoimprint technology, especially in the UV-curable nanoimprint technology that has gradually become the mainstream of imprint technology, low viscosity, high resolution, high etching selectivity UV light Curing thin film materials has become the key to affect the fidelity of imprinted patterns and the fabrication of high aspect ratio structures. Currently, the imprint materials used in UV-curable nanoimprint technology are mainly acrylate photocrosslinkable polymers. The acrylate UV prepolymer has a fast curing rate, but it cannot be cured in an oxygen environment, and has a large volume shrinkage after curing.
美国专利US6334960公开了一种紫外光固化纳米压印技术-步进闪光压印技术，它采用粘度低、流动性好的可紫外光固化丙烯酸类预聚物体系作为纳米压印胶，当模板和可紫外光固化高分子预聚物接触后，不需要外界压力，利用液体特有的毛细现象，就可使紫外光固化材料很容易地注入模板的纳米结构内，并通过紫外光使其快速固化，从而使压印过程可以在室温、很低的压力下迅速完成，从而实现规模化生产。U.S. Patent No. 6,334,960 discloses a UV-curable nano-imprinting technology-step flash imprinting technology, which uses a UV-curable acrylic prepolymer system with low viscosity and good fluidity as a nano-imprinting adhesive. When the template and After contacting the UV-curable polymer prepolymer, no external pressure is needed, and the unique capillary phenomenon of the liquid can be used to easily inject the UV-curable material into the nanostructure of the template, and it can be quickly cured by UV light. As a result, the imprinting process can be completed rapidly at room temperature and under very low pressure, thereby realizing large-scale production.
中国专利CN200610088466.7公开了一种可用于纳米压印也可用于光刻技术的紫外光固化复合材料，反应基团为乙烯基醚、环氧和丙烯酸酯类活性基团，通过在材料中加入含硅材料来提高该层材料对氧等离子刻蚀的选择性，实现双层紫外光固化纳米压印。Chinese patent CN200610088466.7 discloses a UV-curable composite material that can be used for nanoimprinting and photolithography. The reactive groups are vinyl ether, epoxy and acrylate reactive groups. By adding A silicon-containing material is used to improve the selectivity of the layer material to oxygen plasma etching, and to realize double-layer UV-curable nanoimprinting.
CN200810204674.8公开了一种紫外纳米压印用含硅（甲基）丙烯酸酯型光固化压印胶，由（甲基）丙烯酸酯型单体、含硅（甲基）丙烯酸酯、光引发剂、交联剂与助剂组成，通过在传递层旋涂一层压印胶，经过反应离子刻蚀后，可将压印图案转移至基底。CN200810204674.8 discloses a silicon-containing (meth)acrylate photocurable embossing adhesive for ultraviolet nanoimprinting, which consists of (meth)acrylate monomer, silicon-containing (meth)acrylate, photoinitiator , cross-linking agent and auxiliary agent, by spin-coating a layer of embossing glue on the transfer layer, and after reactive ion etching, the embossing pattern can be transferred to the substrate.
由于现有的丙烯酸酯类紫外光纳米压印材料不能在空气中固化，从而在压印时薄膜边缘会存在不固化成分，也不利于纳米压印技术与其它技术（如软压印技术）相结合，因此，需要提供一种可在空气中快速完全固化、高分辨率、高氧气刻蚀选择性的紫外光固化纳米压印材料，从而提高纳米压印技术与其它微纳加工工艺的兼容性，经济高效地产出关键尺寸小于100纳米的图案。Since the existing acrylate UV nanoimprinting materials cannot be cured in the air, there will be uncured components at the edge of the film during imprinting, which is not conducive to the comparison between nanoimprinting technology and other technologies (such as soft imprinting technology). In combination, therefore, it is necessary to provide a UV-curable nanoimprint material that can be rapidly and completely cured in air, high resolution, and high oxygen etching selectivity, thereby improving the compatibility of nanoimprint technology with other micro-nano fabrication processes , to cost-effectively produce patterns with critical dimensions less than 100 nm.
发明内容Contents of the invention
本发明要解决的技术问题是：克服现有丙烯酸酯类紫外光纳米压印材料的不足，提供可在空气中快速完全固化、高分辨率、高氧气刻蚀选择比的紫外光固化纳米压印材料，通过与紫外光固化纳米压印双层压印体系结合，实现与多种微纳加工工艺的兼容，经济高效地产出关键尺寸小于100纳米的图案。The technical problem to be solved by the present invention is to overcome the shortcomings of the existing acrylate UV nanoimprinting materials, and provide UV-curable nanoimprinting materials that can be quickly and completely cured in air, have high resolution, and have a high oxygen etching selectivity ratio. The material, combined with the UV-curable nano-imprint double-layer imprint system, realizes compatibility with various micro-nano processing techniques, and economically and efficiently produces patterns with critical dimensions less than 100 nanometers.
本发明的技术解决方案为：一种巯基-烯紫外光固化纳米压印材料，由低粘度、多官能度的液体预聚物、稀释剂、光引发剂与助剂组成，紫外光固化后体积收缩率小于5%。低粘度、多官能度的液体预聚物由（含硅）巯基单体和（含硅）烯烃单体组成。（含硅）巯基单体质量占液体预聚物质量10%-90%，（含硅）烯烃单体组成占液体预聚物质量90%-10%。所述（含硅）巯基单体和（含硅）烯烃单体均含有两个或两个以上的可固化交联官能团，可固化交联官能团为巯基或碳碳不饱和双键。巯基包括但不限于巯基烷烃、巯基芳香烃、巯基乙酸酯以及巯基丙酸酯。碳碳不饱和双键包括但不限于乙烯基、乙烯基醚、丙烯基醚、烯丙基醚、丙烯酸酯、甲基丙烯酸酯、苯乙烯、N-乙烯基酰胺、共轭二烯、丙烯腈、烯丙基三聚异氰酸酯、烯丙基三嗪、不饱和酯、马来酰亚胺。液体预聚物占预聚物与稀释剂总质量的5%-90%。所述稀释剂是非反应性的溶剂或反应性单体。非反应性溶剂包括但不限于戊烷、己烷、庚烷、辛烷、氯苯、甲苯、二甲苯、丙酮、甲乙酮、甲基异丁酮、甲酸酯、乙酸乙酯、二甲基甲酰胺以及它们的混合物；反应性单体包括但不限于丙烯酸甲酯、丙烯酸乙酯、丙烯酸丁酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸丁酯、甲基乙烯基醚、乙基乙烯基醚以及他们的混合物。稀释剂质量占材料总质量的95%-10%。所述光引发剂选自安息香乙醚、安息香双甲醚、安息香丁醚、联苯甲酰、二苯甲酮的一种或几种。光引发剂质量为液体预聚物质量的0.1%-5%。所述助剂选自有机氟硅烷流平剂、含氟表面活性剂、有机醇、聚醚烷基共改性硅油消泡剂的一种或几种。助剂质量为液体预聚物质量的0.01%-10%。The technical solution of the present invention is: a mercapto-ene UV-curable nanoimprint material, which is composed of a low-viscosity, multifunctional liquid prepolymer, diluent, photoinitiator and auxiliary agent, and the volume after UV-curing The shrinkage rate is less than 5%. Low viscosity, multifunctional liquid prepolymer composed of (silicon-containing) mercapto monomers and (silicon-containing) olefin monomers. The (silicon-containing) mercapto monomer accounts for 10%-90% of the liquid prepolymer mass, and the (silicon-containing) olefin monomer accounts for 90%-10% of the liquid prepolymer mass. Both the (silicon-containing) mercapto monomer and the (silicon-containing) olefin monomer contain two or more curable crosslinking functional groups, and the curable crosslinking functional groups are mercapto groups or carbon-carbon unsaturated double bonds. Mercapto groups include, but are not limited to, mercaptoalkanes, mercaptoarenes, mercaptoacetates, and mercaptopropionates. Carbon-carbon unsaturated double bonds include but not limited to vinyl, vinyl ether, propenyl ether, allyl ether, acrylate, methacrylate, styrene, N-vinylamide, conjugated diene, acrylonitrile , Allyl isocyanate, allyl triazine, unsaturated ester, maleimide. The liquid prepolymer accounts for 5%-90% of the total mass of the prepolymer and diluent. The diluents are non-reactive solvents or reactive monomers. Non-reactive solvents include, but are not limited to, pentane, hexane, heptane, octane, chlorobenzene, toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, formate, ethyl acetate, dimethyl form Amides and mixtures thereof; reactive monomers include but are not limited to methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, methyl vinyl ether, Ethyl vinyl ether and their mixtures. The mass of diluent accounts for 95%-10% of the total mass of the material. The photoinitiator is selected from one or more of benzoin ether, benzoin dimethyl ether, benzoin butyl ether, dibenzoyl, and benzophenone. The mass of the photoinitiator is 0.1%-5% of the mass of the liquid prepolymer. The auxiliary agent is selected from one or more of organofluorosilane leveling agents, fluorine-containing surfactants, organic alcohols, and polyether alkyl co-modified silicone oil defoamers. The additive mass is 0.01%-10% of the liquid prepolymer mass.
所述液体预聚物由（含硅）巯基单体和（含硅）烯烃单体组成，在室温下的动力粘度为1厘泊-10000厘泊。含硅巯基单体为巯基终端或侧链含有巯基的长链硅氧烷、巯基硅烷或巯基接枝笼状硅氧烷，巯基单体为三巯基丙酸酯烷烃、四巯基丙酸酯烷烃或巯基丙酸酯三嗪，含硅烯烃单体为碳碳不饱和双键终端或侧链含有碳碳不饱和双键的长链硅氧烷、乙烯基硅烷或碳碳不饱和双键接枝笼状硅氧烷，烯烃单体为三烯丙基醚烷烃、三烯丙基醚烷基醇、烯丙基三聚异氰酸酯或烯丙基三嗪。所述含硅单体质量占液体预聚物质量的10%-90%。The liquid prepolymer is composed of (silicon-containing) mercapto monomer and (silicon-containing) olefin monomer, and has a dynamic viscosity of 1 centipoise-10000 centipoise at room temperature. Silicon-containing mercapto monomers are long-chain siloxanes, mercaptosilanes, or mercapto-grafted caged siloxanes with mercapto terminals or side chains, and mercapto monomers are trimercaptopropionate alkane, tetramercaptopropionate alkane or Mercapto propionate triazine, the silicon-containing olefin monomer is a long-chain siloxane, vinyl silane or carbon-carbon unsaturated double-bond grafted cage with carbon-carbon unsaturated double bond terminal or side chain containing carbon-carbon unsaturated double bond siloxane, the olefin monomer is triallyl ether alkane, triallyl ether alkyl alcohol, allyl isocyanate or allyl triazine. The mass of the silicon-containing monomer accounts for 10%-90% of the mass of the liquid prepolymer.
一种巯基-烯紫外光固化纳米压印材料的应用，应用于紫外光固化纳米压印工艺，通过旋转涂膜工艺在石英、硅、高分子聚合物等光滑表面上形成一层均匀的液体薄膜，厚度20纳米-500纳米；通过纳米压印工艺在液体薄膜上形成微纳结构图案，进而转化为金属或半导体结构。The application of a mercapto-ene UV-curable nano-imprint material, which is applied to the UV-curable nano-imprint process, forms a uniform liquid film on smooth surfaces such as quartz, silicon, and high molecular polymers through a spin-coating process , with a thickness of 20 nanometers to 500 nanometers; a micro-nano structure pattern is formed on a liquid film through a nanoimprint process, and then transformed into a metal or semiconductor structure.
上述紫外光固化纳米压印工艺，其特点是：基于双层胶体系在基片上制备微纳结构，上层可紫外光固化纳米压印胶为巯基-烯紫外光固化纳米压印材料，膜厚20纳米至200纳米；下层为热塑型高分子聚合物传递层，膜厚200纳米至1000纳米；所述高分子聚合物传递层材料为聚甲基丙烯酸甲酯、聚苯乙烯或聚碳酸酯的一种。The above-mentioned UV-curable nano-imprinting process is characterized in that micro-nano structures are prepared on the substrate based on a double-layer adhesive system, and the upper UV-curable nano-imprinting adhesive is a mercapto-ene UV-curable nano-imprinting material with a film thickness of 20 Nanometer to 200 nanometers; the lower layer is a thermoplastic polymer transfer layer with a film thickness of 200 nanometers to 1000 nanometers; the polymer transfer layer material is polymethyl methacrylate, polystyrene or polycarbonate A sort of.
双层胶体系中，固化后的上层可紫外光固化纳米压印胶与下层高分子聚合物传递层在氧气中的反应离子刻蚀速率之比大于1：5，上层可紫外光固化纳米压印胶上低深宽比的纳米图案通过等离子体刻蚀可传递到下层高分子聚合物传递层，并且结构深宽比大幅增加。In the double-layer adhesive system, the ratio of the reactive ion etching rate of the cured upper UV-curable nano-imprint adhesive to the lower polymer transfer layer in oxygen is greater than 1:5, and the upper UV-curable nano-imprint The low-aspect-ratio nanopatterns on the glue can be transferred to the underlying polymer transfer layer through plasma etching, and the structure's aspect ratio is greatly increased.
下层高分子聚合物传递层，可以在有机溶剂中溶解。高深宽比结构在高分子聚合物传递层形成后，沉积金属或半导体材料，使用有机溶剂除去高分子聚合物传递层，可将传递层结构转化为金属或半导体结构。所述有机溶剂包括但不限于丙酮、甲醇、乙醇以及氯苯。The lower polymer transfer layer can be dissolved in organic solvents. In the high aspect ratio structure, after the polymer transfer layer is formed, metal or semiconductor materials are deposited, and the polymer transfer layer is removed with an organic solvent, so that the transfer layer structure can be transformed into a metal or semiconductor structure. The organic solvent includes but not limited to acetone, methanol, ethanol and chlorobenzene.
本发明与现有技术相比的优点在于：提供一种可在空气中快速完全固化、高分辨率、高氧气刻蚀选择性的紫外光固化纳米压印材料，不需要真空或氮气保护，即可实现纳米压印过程，也可在软压印工艺中应用，基于旋转涂膜和紫外光固化纳米压印双层胶体系，形成高深宽比聚合物结构，进而通过薄膜沉积与传递层溶解，在基片上形成金属或半导体微纳结构。Compared with the prior art, the present invention has the advantages of providing a UV-curable nanoimprint material that can be quickly and completely cured in air, has high resolution, and high oxygen etching selectivity, without the need for vacuum or nitrogen protection, that is, It can realize the nanoimprinting process, and can also be applied in the soft imprinting process. Based on the spin-coating and UV-curing nanoimprinting double-layer adhesive system, a high aspect ratio polymer structure is formed, and then dissolved by thin film deposition and transfer layer. Metal or semiconductor micro-nano structures are formed on the substrate.
附图说明Description of drawings
图1为本实施例中应用配方1制备的金属图案，最小线宽2微米；Fig. 1 is the metal pattern prepared by formula 1 in this embodiment, the minimum line width is 2 microns;
图2为本实施例中配方2压印后获得的图案扫描电子显微镜照片，特征尺寸200纳米；Fig. 2 is the scanning electron micrograph of pattern obtained after formula 2 embossing in the present embodiment, characteristic size is 200 nanometers;
图3为本实施例中配方3压印后获得的图案扫描电子显微镜照片，周期320纳米；Fig. 3 is the scanning electron micrograph of the pattern obtained after formula 3 is embossed in the present embodiment, period 320 nanometers;
图4为本实施例中配方4压印后获得的图案，最小线宽5微米，内插为台阶仪扫描结果；Fig. 4 is the pattern obtained after the embossing of formula 4 in this embodiment, the minimum line width is 5 microns, and the interpolation is the result of spherometer scanning;
图5为本实施例中配方5压印后获得的图案，光栅周期1.5微米；Fig. 5 is the pattern obtained after formula 5 is embossed in this embodiment, and the grating period is 1.5 microns;
图6为本实施例中配方6在石英衬底上压印结果的照片，线宽20微米；Fig. 6 is the photo of formula 6 embossing result on quartz substrate in the present embodiment, line width 20 microns;
图7为本实施例中配方7压印后获得的图案，最小线宽2微米。Fig. 7 is the pattern obtained after embossing of formula 7 in this example, with a minimum line width of 2 microns.
具体实施方式detailed description
以下的实施例仅限于解释本发明，本发明的保护范围应包括权利要求的全部内容，而且通过以下实施例本领域技术人员即可以实现本发明权利要求的全部内容。The following embodiments are limited to explain the present invention, and the protection scope of the present invention should include the entire contents of the claims, and those skilled in the art can realize the entire contents of the claims of the present invention through the following examples.
配方1Recipe 1
实施例1：Example 1:
配方1中巯基-烯紫外光固化纳米压印材料的应用：Application of mercapto-ene UV-curable nanoimprint materials in formulation 1:
将聚甲基丙烯酸甲酯溶解在氯苯中，质量分数为8%，在硅片上旋转成膜，得到250纳米厚度的传递层，180℃烘烤2分钟。Polymethyl methacrylate was dissolved in chlorobenzene with a mass fraction of 8%, and it was spin-formed on a silicon wafer to obtain a transfer layer with a thickness of 250 nm, and baked at 180°C for 2 minutes.
将配方1中各组分混合均匀，旋涂在聚甲基丙烯酸甲酯传递层上，厚度为180纳米。The components in formula 1 were mixed evenly, and spin-coated on the polymethyl methacrylate transfer layer with a thickness of 180 nm.
在0.5个大气压压力下进行紫外光固化纳米压印，固化后移去模板。The UV-cured nanoimprint was carried out under 0.5 atmospheric pressure, and the template was removed after curing.
在三氟甲烷与氧气流量比为2：1的反应离子刻蚀条件下将压印残余层除去，然后通过氧气反应离子刻蚀将结构传递至传递层，并露出基片。The residual imprinting layer was removed under the condition of reactive ion etching with the flow ratio of trifluoromethane and oxygen at 2:1, and then the structure was transferred to the transfer layer by oxygen reactive ion etching, and the substrate was exposed.
热蒸镀金属层，将基片放入丙酮溶液超声5分钟，得到与压印模板相同的金属结构。The metal layer is thermally evaporated, and the substrate is placed in an acetone solution for 5 minutes to obtain the same metal structure as the embossed template.
图1为本实施例中应用配方1制备的金属图案，最小线宽2微米。Fig. 1 is a metal pattern prepared by applying formula 1 in this example, with a minimum line width of 2 microns.
实施例2Example 2
配方2Recipe 2
图2为本实施例中配方2压印后获得的图案扫描电子显微镜照片，特征尺寸200纳米。Fig. 2 is a scanning electron micrograph of the pattern obtained after imprinting of formula 2 in this example, with a feature size of 200 nanometers.
实施例3Example 3
配方3Recipe 3
图3为本实施例中配方3压印后获得的图案扫描电子显微镜照片，周期320纳米。Fig. 3 is a scanning electron micrograph of a pattern obtained after imprinting of formula 3 in this example, with a period of 320 nanometers.
实施例4Example 4
配方4Recipe 4
图4为本实施例中配方4压印后获得的图案，最小线宽5微米，内插为台阶仪扫描结果。Fig. 4 is the pattern obtained after embossing of formula 4 in this embodiment, the minimum line width is 5 microns, and the interpolation is the result of spheroid scanning.
实施例5Example 5
配方5Recipe 5
图5为本实施例中配方5压印后获得的图案，光栅周期1.5微米。Fig. 5 is the pattern obtained after embossing of formula 5 in this embodiment, and the grating period is 1.5 microns.
实施例6Example 6
配方6Recipe 6
图6为本实施例中配方6在石英衬底上压印结果的照片，线宽20微米。Fig. 6 is a photograph of the embossing result of formulation 6 on a quartz substrate in this example, with a line width of 20 microns.
实施例7Example 7
配方7Recipe 7
图7为本实施例中配方7压印后获得的图案，最小线宽2微米。Fig. 7 is the pattern obtained after embossing of formula 7 in this example, with a minimum line width of 2 microns.
需要说明的是，按照本发明上述实施例，本领域技术人员是完全可以实现本发明独立权利要求及从属权利的全部范围的，实现过程及方法同上述实施例；且本发明未详细阐述部分属于本领域公知技术。It should be noted that, according to the above-mentioned embodiments of the present invention, those skilled in the art can fully realize the entire scope of the independent claims and dependent rights of the present invention, and the implementation process and method are the same as the above-mentioned embodiments; and the parts not described in detail in the present invention belong to Known techniques in the art.
以上所述，仅为本发明部分具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本领域的人员在本发明揭露的技术范围内，可轻易想到的变化或替换，都应涵盖在本发明的保护范围之内。The above are only some specific implementations of the present invention, but the protection scope of the present invention is not limited thereto. Any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope disclosed in the present invention should be covered within the protection scope of the present invention.
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310234613.7ACN103279011B (en) | 2013-06-14 | 2013-06-14 | Sulfydryl-alkene ultraviolet curing nanoimprint lithography material |
| Application Number | Priority Date | Filing Date | Title |
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| CN201310234613.7ACN103279011B (en) | 2013-06-14 | 2013-06-14 | Sulfydryl-alkene ultraviolet curing nanoimprint lithography material |
| Publication Number | Publication Date |
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| CN103279011A CN103279011A (en) | 2013-09-04 |
| CN103279011Btrue CN103279011B (en) | 2016-03-30 |
| Application Number | Title | Priority Date | Filing Date |
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| CN201310234613.7AActiveCN103279011B (en) | 2013-06-14 | 2013-06-14 | Sulfydryl-alkene ultraviolet curing nanoimprint lithography material |
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