CN116003665B - Polymer and preparation method of 193nm photoetching top coating film containing same - Google Patents
Polymer and preparation method of 193nm photoetching top coating film containing same Download PDFInfo
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- CN116003665B CN116003665B CN202111231202.3A CN202111231202A CN116003665B CN 116003665 B CN116003665 B CN 116003665B CN 202111231202 A CN202111231202 A CN 202111231202A CN 116003665 B CN116003665 B CN 116003665B
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Abstract
The invention discloses a polymer and a preparation method of a top coating film containing the same for 193nm photoetching. The polymer is obtained by polymerizing a monomer shown in a formula A, a monomer shown in a formula B and a monomer shown in a formula L; the top coat film comprising the polymer has at least any one of the following advantages: better solubility, higher resistance to pure water, and high pattern resolution.
Description
Technical Field
The invention relates to a polymer and a preparation method of a 193nm photoetching top coating film containing the same.
Background
In recent years, with the development of digital devices such as computers, the processing amount of processing operation data and two-dimensional and three-dimensional image data has been gradually increased, and in order to rapidly process these information, a large-capacity and high-speed memory and a high-performance microprocessor have been required. Further, with the development of networks such as the internet and the like, the increase in bandwidth has been accelerated, and it has been expected that the processing power required for digital devices will be increased.
In order to meet this demand, various equipment such as semiconductor devices are required to have higher density and higher integration. Among them, a process technique having a minimum line width of 0.13 μm or less is required for manufacturing a DRAM having an integration level of 1Gbit or more because of severe requirements for a photolithography technique capable of micromachining, and a photolithography method using ArF excimer laser (193 nm) is used in response to this. Further, in order to process a fine pattern, development of lithography using Extreme Ultraviolet (EUV) has been performed.
In these wavelength regions, novolak (novolacs) and polyvinyl phenol resins, which have been conventionally used for resist compositions, have not been used because of excessive light absorption.
Along with the miniaturization of the device structure, not only the change of the light source but also the improvement of the exposure apparatus have been studied. For example, a stepper (reduced projection exposure apparatus) has a significantly improved resolution by improving the performance of a reduced projection lens and improving the design of an optical system. The performance of the lens used in the stepper is expressed as NA (aperture number), but a value of around 0.9 in air is considered as a physical limit, which is now reached. Therefore, attempts to increase NA to 1.0 or more by filling the space between the lens and the wafer with a medium having a higher refractive index than air, particularly exposure techniques based on an immersion system using pure water (hereinafter, sometimes simply referred to as water) as a medium have been attracting attention.
In immersion lithography, various problems are pointed out as the resist film is in contact with a medium (e.g., water). In particular, the following problems exist: an acid generated in the film by exposure, an amine compound added as a quencher, is dissolved in water, thereby causing a change in pattern shape; pattern collapse due to swelling, and the like. Providing a top coat over the resist is one solution.
Disclosure of Invention
In view of the foregoing problems of the prior art, the present invention is directed to a polymer and a method for preparing a 193nm lithography top coating film containing the same, which has at least any of the following advantages: better solubility, higher resistance to pure water, and high pattern resolution.
The invention provides a polymer, and a preparation method of the polymer comprises the following steps: polymerizing a monomer shown in a formula A, a monomer shown in a formula B and a monomer shown in a formula L;
in the preparation method of the polymer, the weight part of the monomer shown in the formula A is 2-10 parts, preferably 2 parts, 4 parts, 5 parts, 8 parts or 10 parts.
In the preparation method of the polymer, the weight part of the monomer shown in the formula B is 1-6 parts, preferably 1 part, 1.5 parts, 2 parts, 3.5 parts or 6 parts.
In the preparation method of the polymer, the weight part of the monomer shown in the formula L is 1-4 parts, preferably 1 part, 1.5 parts, 2.5 parts or 4 parts.
In one embodiment of the invention, the weight average molecular weight (Mw) of the polymer may be 8000 to 12000, preferably 8848, 9674, 9933, 10212 or 11182.
In one embodiment of the invention, the polymer may be selected from any one of the following polymers P1-P5:
polymer P1: the weight part of the monomer shown in the formula A is 2 parts, the weight part of the monomer shown in the formula B is 1.5 parts, and the weight part of the monomer shown in the formula L is 1 part;
polymer P2: the weight part of the monomer shown in the formula A is 4 parts, the weight part of the monomer shown in the formula B is 1 part, and the weight part of the monomer shown in the formula L is 1.5 parts;
polymer P3: the weight part of the monomer shown in the formula A is 5 parts, the weight part of the monomer shown in the formula B is 2 parts, and the weight part of the monomer shown in the formula L is 1 part;
polymer P4: the weight part of the monomer shown in the formula A is 8 parts, the weight part of the monomer shown in the formula B is 3.5 parts, and the weight part of the monomer shown in the formula L is 2.5 parts;
polymer P5: the weight part of the monomer shown in the formula A is 10 parts, the weight part of the monomer shown in the formula B is 6 parts, and the weight part of the monomer shown in the formula L is 4 parts.
In the polymer P1, the weight average molecular weight of the polymer may be 11182.
In the polymer P2, the weight average molecular weight of the polymer may be 10242.
In the polymer P3, the weight average molecular weight of the polymer may be 8848.
In the polymer P4, the weight average molecular weight of the polymer may be 9674.
In the polymer P5, the weight average molecular weight of the polymer may be 9933.
In one embodiment of the present invention, the method for preparing the polymer preferably comprises the steps of: the monomer shown in the formula A, the monomer shown in the formula B and the monomer shown in the formula L are polymerized under the action of an initiator in an organic solvent to obtain the polymer.
In the preparation method of the polymer, the organic solvent may be a conventional organic solvent for such polymerization reaction in the art, preferably a ketone solvent such as methyl ethyl ketone.
In the preparation of the polymer, the initiator may be a conventional reaction of this type in the art, preferably azo-type initiator, such as azobisisobutyronitrile.
In the preparation method of the polymer, the weight part of the organic solvent may be conventional in this type of reaction in the art, preferably 10 to 20 parts, more preferably 15 parts.
In the preparation method of the polymer, the weight part of the initiator is conventional in the art, preferably 0.05-0.3 part, more preferably 0.1 part.
In the preparation method of the polymers P1 to P5, it is preferable to carry out the polymerization in the presence of 0.1 part of azobisisobutyronitrile and 15 parts of methyl ethyl ketone.
The polymerization reaction may be conventional in the art, and is preferably carried out under an inert gas (e.g., nitrogen).
In the preparation of the polymer, the polymerization reaction temperature may be conventional in the art, preferably 60-90 ℃, for example 70 ℃.
In the preparation method of the polymer, the polymerization reaction time may be a time conventional in the art, for example, 8 to 20 hours, and further, for example, 12 hours.
In the method of preparing the polymer, the polymerization reaction may further include a post-treatment step such as one or more of cooling, precipitation and drying.
Among them, the organic solvent used in the precipitation may be a conventional reaction of this type in the art, and an alkane solvent such as n-hexane is preferred. Preferably, the parts by weight of the organic solvent may be conventional in this type of reaction, preferably 40-70 parts, preferably 50 parts.
Wherein the drying may be conventional in the art, preferably vacuum drying, e.g. at 50 ℃ for 24 hours.
The invention also provides a preparation method of the polymer, which comprises the following steps: polymerizing a monomer shown in a formula A, a monomer shown in a formula B and a monomer shown in a formula L;
wherein each operation and condition is as described above.
The present invention also provides a top coat film made from a composition comprising a polymer as described above and a solvent as described above.
In one embodiment of the invention, the thickness of the top coat film may be conventional in this type of reaction, preferably 20-200nm, e.g. 50nm.
The invention provides a preparation method of a top coating film, which comprises the steps of coating a top coating solution on the surface of a silicon wafer and drying; the topcoat solution includes a polymer as described above and a solvent.
In the method of preparing the top coat film, the mass percent (wt%) of the polymer in the top coat solution may be conventional in this type of reaction in the art, preferably 2wt% to 4wt%, preferably 3wt%.
In the method for producing the top coat film, the top coat solution is preferably filtered using a membrane filter, more preferably, the pore size of the membrane filter is 0.2 μm, before coating.
In the method of preparing the top coat film, the drying temperature may be a conventional drying temperature in the art, for example, 50 to 120 ℃, and still for example, 100 ℃.
In the method of producing the top coat film, the drying time may be a drying time conventional in the art, for example, 50 to 200 seconds, and further, for example, 90 seconds.
In the method of preparing the top coat film, the coating may be a conventional coating method used in the art for forming a photolithographic pattern, such as spin coating. The spin coating may be conventional in this type of reaction, preferably using a spin coater at 1500 rpm.
The present invention also provides a dual resin film comprising the top coat film and the resist film as described above.
The invention also provides a preparation method of the dual resin film, which comprises the steps of coating the top coating solution on the surface of the corrosion-resistant film and drying. The resist film may be a conventional resist film in the art, wherein the preparation method thereof preferably comprises the steps of: and (3) coating the resist solution on the surface of the silicon wafer, and drying. The resist solution generally includes a photoresist and a photoacid generator. Preferably, the photoresist is tai-6990PH, available from TOK. The photoacid generator was triphenylsulfonium triflate, purchased from Midori Kagaku co.
In the method of producing the resist film, the coating may be conventional in this type of reaction in the art, and spin coating is preferred.
In the method for producing a resist film, the resist film solution is preferably filtered using a film filter, and more preferably, the film filter has a pore diameter of 0.2 μm.
In the method of producing the resist film, the drying temperature may be a conventional drying temperature used in the art for forming a top resist film, for example, 50 to 120 ℃, and still more for example, 100 ℃.
In the method of producing the resist film, the drying time may be a conventional drying time used in the art for forming a top resist film, for example, 50 to 200 seconds, and further, for example, 90 seconds.
In the method for producing the resist film, the thickness of the resist film may be conventional in this type of reaction in the art, preferably 20 to 200nm, for example 150nm.
On the basis of conforming to the common knowledge in the field, the above preferred conditions can be arbitrarily combined to obtain the preferred examples of the invention.
The reagents and materials used in the present invention are commercially available.
The invention has the positive progress effects that: the top coat film has at least any one of the following advantages: better solubility, higher resistance to pure water, and high pattern resolution.
Detailed Description
The invention is further illustrated by means of the following examples, which are not intended to limit the scope of the invention. The experimental methods, in which specific conditions are not noted in the following examples, were selected according to conventional methods and conditions, or according to the commercial specifications.
Preparation of the Polymer
To a glass flask equipped with a condenser, A, B (comparative example, B was replaced with C), 0.1 part of L, 0.1 part of azobisisobutyronitrile, and 15 parts of methyl ethyl ketone were added in parts by weight, and the flask was placed under a nitrogen atmosphere. The solution was warmed to 70℃and stirred for 12 hours. After the completion of the reaction, the mixture was poured into 50 parts of n-hexane and stirred, and the resulting precipitate was taken out. This was dried at 50℃for 24 hours to form a white solid, and a polymer was obtained, and the molecular weight was calculated by gel permeation chromatography (GPC, standard substance: polystyrene).
TABLE 1
| A | B | C | L | Mw | |
| Polymer P1 | 2 | 1.5 | - | 1 | 9423 |
| Polymer P2 | 4 | 1 | - | 1.5 | 11882 |
| Polymer P3 | 5 | 2 | - | 1 | 9866 |
| Polymer P4 | 8 | 3.5 | - | 2.5 | 10828 |
| Polymer P5 | 10 | 6 | - | 4 | 11065 |
| Comparative Polymer CP1 | 2 | - | 1.5 | 1 | 11665 |
| Comparative Polymer CP2 | 4 | - | 1 | 1.5 | 8354 |
| Comparative Polymer CP3 | 5 | - | 2 | 1 | 8055 |
| Comparative Polymer CP4 | 8 | - | 3.5 | 2.5 | 8056 |
| Comparative Polymer CP5 | 10 | - | 6 | 4 | 9956 |
Effect examples
Preparation of the Top coat solution
100 parts by mass of the synthesized polymer was dissolved in 900 parts by mass of 4-methyl-2-pentanol (MIBC) as a solvent, and the concentration was adjusted to 3wt% with the same solvent, resulting in a uniform and transparent top coating solution.
Production of Top coat film
After each of the top coat solutions was filtered by a membrane filter (0.2 μm), it was spin-coated on a silicon wafer at a spin rate of 1,500rpm using a spin coater, and dried at 80℃for 90 seconds on a hot plate, to obtain a uniform top coat film of about 50nm on the silicon wafer.
Advancing contact angle/receding contact angle evaluation test
For the top coat film formed on the silicon wafer, the advancing contact angle and the receding contact angle of the water drop were measured by the expansion/contraction method using a device CA-X model manufactured by the co-ordinates surface science at 20 ℃.
Alkaline developer solubility test
For the top coat film formed on the silicon wafer, the dissolution rate in a 2.38 mass% aqueous tetramethylammonium hydroxide solution (alkaline developer) was measured at 20℃using a resist development analyzer RDA-790 (manufactured by Litho Tech Japan Corporation).
Preparation of resist/Top coat bilayer resin film
A resist solution (photoresist: TOK-manufactured Tai-6990PH, photoacid generator: midori Kagaku Co., ltd., manufactured by triphenylsulfonium triflate) was spin-coated on a silicon wafer using a spin coater, and then dried at 100℃for 90 seconds on a hot plate to form a resist film having a film thickness of about 150nm. After spin-coating the top coat solution filtered by a film filter (0.2 μm) on the resist film using a spin coater, the solution was dried at 80℃for 90 seconds on a hot plate to form a double-layer resin film (a double-layer film composed of a resist layer and a top coat layer) having an overall film thickness of about 200 nm.
The following pure water immersion treatment and exposure analysis test were performed on the double-layer resin film formed on the silicon wafer.
Pure water immersion test
The obtained 20 silicon wafers each having a bilayer resin film (bilayer film comprising a resist layer and a top coat layer) were immersed in 20ml of pure water at 20 ℃ for 10 minutes, and after the extract was extracted, the extract was measured by ion chromatography to confirm the presence or absence of the extract. No peaks ascribed to photoacid generators or their decomposition products were detected except for samples without the top coat. By providing the top coat layer, dissolution of the resist component in water is suppressed.
Exposure resolution (Pattern formation) test
A double-layer resin film (double-layer film composed of a resist layer and a top coat layer) silicon wafer, which was pre-baked at 80 ℃ for 90 seconds, was exposed to light at 193nm via a photomask. While rotating the exposed wafer, pure water was added dropwise for 2 minutes. Then, the resist was baked at 120℃for 60 seconds after exposure, and developed with an alkaline developer. As the alkaline developer, a 2.38 mass% aqueous tetramethylammonium hydroxide solution was used. The cross section of the obtained pattern was observed by a scanning electron microscope, and the pattern resolution was characterized by the degree of distortion of the rectangle.
TABLE 2
Conclusion: referring to Table 2, the top coat films prepared using the polymers P1 to P5 had higher slip angles and higher receding contact angles and faster dissolution rates than the top coat of the comparative example. In addition, the bilayer film prepared in the examples has strong stability and excellent pattern resolution.
Claims (12)
1. A polymer, characterized in that the method of preparing the polymer comprises the steps of: polymerizing a monomer shown in a formula A, a monomer shown in a formula B and a monomer shown in a formula L;
in the preparation method of the polymer, the weight part of the monomer shown in the formula A is 2-10 parts;
in the preparation method of the polymer, the weight part of the monomer shown in the formula B is 1-6 parts;
in the preparation method of the polymer, the weight part of the monomer shown in the formula L is 1-4 parts by weight 。
2. The polymer of claim 1, wherein the polymer has a weight average molecular weight of 8000 to 12000 in the process for preparing the polymer.
3. The polymer of claim 2, wherein the monomer of formula a is present in an amount of 2 parts, 4 parts, 5 parts, 8 parts, or 10 parts by weight;
and/or, in the preparation method of the polymer, the weight part of the monomer shown in the formula B is 1 part, 1.5 parts, 2 parts, 3.5 parts or 6 parts;
and/or, in the preparation method of the polymer, the weight part of the monomer shown in the formula L is 1 part, 1.5 parts, 2.5 parts or 4 parts.
4. The polymer of claim 1, wherein in the process for preparing the polymer,
the polymer P1 is prepared by taking 2 parts by weight of the monomer shown in the formula A, 1.5 parts by weight of the monomer shown in the formula B and 1 part by weight of the monomer shown in the formula L;
or, the weight part of the monomer shown in the formula A is 4 parts, the weight part of the monomer shown in the formula B is 1 part, and the weight part of the monomer shown in the formula L is 1.5 parts; preparing a polymer P2;
or, the weight part of the monomer shown in the formula A is 5 parts, the weight part of the monomer shown in the formula B is 2 parts, and the weight part of the monomer shown in the formula L is 1 part; preparing a polymer P3;
or, the weight part of the monomer shown in the formula A is 8 parts, the weight part of the monomer shown in the formula B is 3.5 parts, and the weight part of the monomer shown in the formula L is 2.5 parts; preparing a polymer P4;
or, the weight part of the monomer shown in the formula A is 10 parts, the weight part of the monomer shown in the formula B is 6 parts, and the weight part of the monomer shown in the formula L is 4 parts; polymer P5 was obtained.
5. The polymer as claimed in claim 4, wherein the preparation of the polymers P1 to P5 is carried out with 0.1 part of azobisisobutyronitrile and 15 parts of methyl ethyl ketone.
6. The polymer of any one of claims 1 to 4, wherein the method of preparing the polymer comprises the steps of: and in an organic solvent, carrying out polymerization reaction on the monomer shown in the formula A, the monomer shown in the formula B and the monomer shown in the formula L under the action of an initiator to obtain the polymer.
7. The polymer of claim 6, wherein in the method of preparing the polymer, the organic solvent is a ketone solvent;
and/or, in the preparation method of the polymer, the initiator is azo initiator;
and/or, in the preparation method of the polymer, the weight part of the organic solvent is 10-20 parts;
and/or, in the preparation method of the polymer, the weight part of the initiator is 0.05-0.3 part by weight;
and/or, in the preparation method of the polymer, the polymerization reaction is carried out under inert gas;
and/or, in the preparation method of the polymer, the temperature of the polymerization reaction is 60-90 ℃;
and/or, in the preparation method of the polymer, the polymerization reaction time is 8-20 hours;
and/or, in the preparation method of the polymer, the post-treatment step is further included after the polymerization reaction.
8. The polymer of claim 6, wherein in the method of preparing the polymer, the organic solvent is ethyl ketone;
and/or, in the preparation method of the polymer, the initiator is azodiisobutyronitrile;
and/or, in the preparation method of the polymer, the weight part of the organic solvent is 15 parts by weight;
and/or, in the preparation method of the polymer, the weight part of the initiator is 0.1 part by weight;
and/or, in the preparation method of the polymer, the temperature of the polymerization reaction is 70 ℃;
and/or, in the method for producing a polymer, the polymerization reaction time is 12 hours;
and/or, in the preparation method of the polymer, a post-treatment step is further included after the polymerization reaction, and the post-treatment step includes one or more of cooling, precipitation and drying.
9. The polymer of claim 8, wherein in the post-treatment step, the organic solvent used in the precipitation is an alkane solvent;
and/or, in the post-treatment step, the drying is vacuum drying.
10. The polymer of claim 9, wherein the alkane solvent is n-hexane;
and/or, the weight portion of the organic solvent is 40-70 portions.
11. The polymer of claim 10, wherein the organic solvent is present in an amount of 50 parts by weight.
12. A method of preparing a polymer comprising the steps of: polymerizing a monomer shown in a formula A, a monomer shown in a formula B and a monomer shown in a formula L;
in the preparation method, each operation and condition are the same as defined in any one of claims 1 to 11.
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