CN113985701A - Negative photoresist composition, preparation method and method for forming photoresist pattern - Google Patents
Negative photoresist composition, preparation method and method for forming photoresist pattern Download PDFInfo
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- CN113985701A CN113985701A CN202111476489.6A CN202111476489A CN113985701A CN 113985701 A CN113985701 A CN 113985701A CN 202111476489 A CN202111476489 A CN 202111476489A CN 113985701 A CN113985701 A CN 113985701A
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 94
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 229920005989 resin Polymers 0.000 claims abstract description 36
- 239000011347 resin Substances 0.000 claims abstract description 36
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 31
- 239000010703 silicon Substances 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 14
- 229920002050 silicone resin Polymers 0.000 claims description 11
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 6
- -1 sulfonic acid compound Chemical class 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 claims description 3
- 238000011161 development Methods 0.000 claims description 3
- 229940116333 ethyl lactate Drugs 0.000 claims description 3
- 238000004528 spin coating Methods 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 238000004806 packaging method and process Methods 0.000 abstract description 7
- 238000012858 packaging process Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 11
- 239000002994 raw material Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- BILNREVJDCLBQF-UHFFFAOYSA-N CC1=C(CCl)N=NN=C1CCl Chemical compound CC1=C(CCl)N=NN=C1CCl BILNREVJDCLBQF-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000001259 photo etching Methods 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- 235000012431 wafers Nutrition 0.000 description 2
- MMZCYVBYIOUFEO-UHFFFAOYSA-N (1,3-dioxoisoindol-2-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON1C(=O)C2=CC=CC=C2C1=O MMZCYVBYIOUFEO-UHFFFAOYSA-N 0.000 description 1
- OKRLWHAZMUFONP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)ON1C(=O)CCC1=O OKRLWHAZMUFONP-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- G03F7/20—Exposure; Apparatus therefor
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention provides a negative photoresist composition, a preparation method and application thereof, and a method for forming a photoresist pattern, and particularly relates to the technical field of photoresist. The negative photoresist composition includes a high-silicon resin and a photosensitive acid generator. The mass ratio of the high-silicon resin to the photosensitive acid generator is 10-70: 0.5-10. The negative photoresist composition provided by the invention uses high-silicon resin with good chemical stability and insulating property, can reduce the dielectric constant of the negative photoresist composition, the dielectric constant is as low as 2.8-3.2, the insulating property requirement of a packaging process can be met, the packaging efficiency and effect can be improved, foreign monopoly is broken, and the production cost is reduced.
Description
Technical Field
The invention relates to the technical field of photoresist, in particular to a negative photoresist composition, a preparation method and a method for forming a photoresist pattern.
Background
Integrated Circuit (IC) packaging is an essential link in the integrated circuit industry chain. Packaging refers to a process of processing a wafer passing a test to obtain an independent chip, so that a circuit chip is protected from the influence of the surrounding environment, the chip is protected, the heat conduction performance is enhanced, and the internal circuit and the external circuit of the chip are communicated. Package testing has become an important component of integrated circuits in our country today.
A critical photosensitive insulating material is required in the package, requiring a material with a dielectric constant below 3.5. In the prior art, polyimide photoresist is adopted to improve the insulating property, the dielectric constant of the polyimide photoresist can reach 3.3-3.6, and no substitute product exists at home.
The existing photoresist can not meet the increasing insulation performance requirement of the photoresist in the packaging process, and the dielectric constant is difficult to continuously decrease.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
One of the objectives of the present invention is to provide a negative photoresist composition, which solves the technical problem of high dielectric constant in the prior art.
The second object of the present invention is to provide a method for producing a negative photoresist composition, which is simple in process, large in throughput, suitable for mass production, and low in cost.
It is a further object of the present invention to provide a negative photoresist composition for use in the manufacture of integrated circuits, which improves the production efficiency and reduces the production cost of integrated circuits.
The fourth objective of the present invention is to provide a method for forming a photoresist pattern, which ensures that the formed pattern meets the actual process requirements and realizes a better photoresist pattern.
In order to solve the technical problems, the invention adopts the following technical scheme:
in a first aspect, the invention provides a negative photoresist composition comprising a high silicon resin and a photosensitive acid generator.
Optionally, the mass ratio of the high-silicon resin to the photosensitive acid generator is 10-70: 0.5-10.
Optionally, the high-silicon resin has a structural formula:
wherein n is an integer greater than 1.
Preferably, the high silicone resin has a molecular weight of 1000-.
Optionally, the photosensitive acid generator comprises a non-ionic acid generator.
Preferably, the non-ionic acid generator comprises a triazine and/or a sulfonic acid compound.
Optionally, a solvent is also included.
Preferably, the solvent comprises an organic solvent.
Preferably, the organic solvent includes at least one of propylene glycol methyl ether, propylene glycol propyl ether, propylene glycol methyl ether acetate, ethyl acetate and ethyl lactate.
The second aspect of the present invention provides a method for preparing the above negative photoresist composition, wherein the high-silicon resin, the photosensitive acid generator and optionally a solvent are uniformly mixed.
In a third aspect, the invention provides the use of a negative photoresist composition as described above in the manufacture of an integrated circuit.
A fourth aspect of the present invention provides a method of forming a photoresist pattern, the method comprising the steps of:
step A: spin coating a negative photoresist composition on a substrate to form a photoresist layer;
and B: pre-baking the photoresist layer, and performing i-line exposure to obtain an exposed photoresist layer;
and C: and baking the exposed photoresist layer and developing to obtain the photoresist pattern.
Optionally, the pre-baking temperature is 90-110 ℃.
Preferably, the pre-baking time is 30-90 s.
Preferably, the temperature of the intermediate drying is 100-.
Preferably, the baking time is 30-90 s.
Optionally, in step B, a pre-bake is performed and the photoresist layer to be exposed is obtained before the i-line exposure.
Preferably, the film thickness of the photoresist layer to be exposed is 2-5 μm.
Preferably, step C adds a developer to perform development.
Preferably, the developer solution comprises a tetramethylammonium hydroxide solution.
Compared with the prior art, the invention has at least the following beneficial effects:
according to the negative photoresist composition provided by the invention, the special chain structure of the high-silicon resin ensures that the negative photoresist composition has good chemical stability and insulating property, and silicon hydroxyl in the resin structure can react and connect with each other under the catalysis of acid to form a negative image, so that the dielectric constant of the negative photoresist composition is reduced to 2.8-3.2, the insulating property requirement of a packaging process can be met, the packaging efficiency and effect can be improved, foreign monopoly can be broken, and the production cost is reduced.
The preparation method of the negative photoresist composition provided by the invention has the advantages of simple process, large processing capacity, suitability for mass production and low cost.
The negative photoresist composition provided by the invention is applied to manufacturing of integrated circuits, and can be applied to packaging of chips with 22nm critical dimension, so that the production efficiency of the integrated circuits is improved, and the production cost is reduced.
The method for forming the photoresist pattern ensures that the formed pattern meets the actual process requirement and realizes a better photoresist pattern.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. The components of embodiments of the present invention may be arranged and designed in a wide variety of different configurations.
According to a first aspect of the invention, there is provided a negative photoresist composition comprising a high silicon resin and a photosensitive acid generator.
The negative photoresist composition provided by the invention uses high-silicon resin with good chemical stability and insulating property, can reduce the dielectric constant of the negative photoresist composition, the dielectric constant is as low as 2.8-3.2, the insulating property requirement of a packaging process can be met, the packaging efficiency and effect can be improved, foreign monopoly is broken, and the production cost is reduced.
Optionally, the mass ratio of the high-silicon resin to the photosensitive acid generator is 10-70: 0.5-10.
When the mass ratio of the high-silicon resin to the photosensitive acid generator is higher than 70:0.5, the resin molecules cannot be well connected due to the fact that the ratio of the acid generator is too low, so that the resin molecules are dissolved in a developing solution and cannot form a photoetching image; when the mass ratio of the high silicone resin to the photosensitive acid generator is less than 10:10, a good photoresist film cannot be formed with a too low ratio of the high silicone resin.
In some preferred embodiments of the invention, the mass ratio of the high silicone resin and the photosensitive acid generator is typically, but not limited to, 10:0.5, 50:0.5, 70:0.5, 10:1, 50:1, 70:1, 10:5, 50:5, 70:5, 10:10, 50:10, or 70: 10.
Optionally, the high-silicon resin has a structural formula:
wherein n is an integer greater than 1.
Preferably, the high silicone resin has a molecular weight of 1000-.
When the molecular weight of the high-silicon resin is less than 1000, the low molecular weight leads to insufficient connection efficiency, macromolecules insoluble in a developing solution are difficult to form, and a photoetching image cannot be formed; when the high silicone resin has a molecular weight of more than 10000, the resin is difficult to dissolve in a developer without linkage due to an excessively high molecular weight, resulting in failure to form a lithographic image.
In some embodiments of the invention, the high silicone resin typically has a molecular weight of, but not limited to, 1000, 2000, 3000, 4000, 5000, 6000, 7000, 8000, 9000, or 10000.
Optionally, the photosensitive acid generator comprises a non-ionic acid generator.
Photosensitive acid generatorIs a light-sensitive compound which decomposes under irradiation to produce an acid (H)+). During the post-exposure and mid-baking (PEB) process, the acids can be used as catalysts to enable the silicon hydroxyl groups on the high-silicon resin to be connected with each other, the resin is not dissolved in the developing solution after the molecular weight of the resin is increased, and the unexposed part can be continuously dissolved in the developing solution due to the fact that the catalysis of the acids is avoided, so that the photoresist forms a negative image after being developed.
Preferably, the nonionic acid generator comprises triazine compounds and/or sulfonic acid compounds, and the molecules of the compounds generated by the nonionic acid generator after illumination can well catalyze the mutual connection of resin molecules.
Triazines include, but are not limited to, methyl bischloromethyl triazine.
Sulfonic acid compounds include, but are not limited to, N-p-toluenesulfonyloxyphthalimide, naphthalimide triflate, p-methoxyphenylacetonitrile p-toluenesulfonate, N-trifluoromethanesulfonyloxysuccinimide, or N-trifluoromethanesulfonyloxynaphthalimide.
Optionally, a solvent is also included.
The solvent dissolves the high-silicon resin therein to form a liquid substance, so that the formed negative photoresist composition has good fluidity and is convenient to cover on a substrate.
Preferably, the solvent comprises an organic solvent.
Preferably, the organic solvent includes at least one of propylene glycol methyl ether, propylene glycol propyl ether, propylene glycol methyl ether acetate, ethyl acetate and ethyl lactate.
According to the second aspect of the present invention, there is provided a method for preparing the above negative photoresist composition, comprising mixing the high-silicon resin, the photosensitive acid generator and optionally a solvent.
The preparation method of the negative photoresist composition provided by the invention has the advantages of simple process, large processing capacity, suitability for mass production and low cost.
In a third aspect, the invention provides the use of a negative photoresist composition as described above in the manufacture of an integrated circuit.
The negative photoresist composition provided by the invention is applied to manufacturing of integrated circuits, and can be applied to packaging of chips with 22nm critical dimension, so that the production efficiency of the integrated circuits is improved, and the production cost is reduced.
A fourth aspect of the present invention provides a method of forming a photoresist pattern, the method comprising the steps of:
step A: spin coating a negative photoresist composition on a substrate to form a photoresist layer;
and B: pre-baking the photoresist layer, and performing i-line exposure to obtain an exposed photoresist layer;
and C: and baking the exposed photoresist layer and developing to obtain the photoresist pattern.
The method for forming the photoresist pattern ensures that the formed pattern meets the actual process requirement and realizes a better photoresist pattern.
Optionally, the pre-baking temperature is 90-110 ℃.
In some embodiments of the invention, the temperature of the pre-bake is typically, but not limited to, 90 ℃, 95 ℃, 100 ℃, 105 ℃, or 110 ℃.
Preferably, the pre-baking time is 30-90 s.
In some embodiments of the invention, the time of the pre-baking is 30s, 40s, 50s, 60s, 70s, 80s or 90 s.
Preferably, the temperature of the intermediate drying is 100-.
In some embodiments of the invention, the temperature of the medium baking is typically, but not limited to, 100 ℃, 105 ℃, 110 ℃, 115 ℃ or 120 ℃.
Preferably, the baking time is 30-90 s.
In some embodiments of the invention, the intermediate baking time is 30s, 40s, 50s, 60s, 70s, 80s, or 90 s.
Optionally, in step B, a pre-bake is performed and the photoresist layer to be exposed is obtained before the i-line exposure.
Preferably, the film thickness of the photoresist layer to be exposed is 2-5 μm.
In some embodiments of the present invention, the film thickness of the photoresist layer to be exposed is typically, but not limited to, 2 μm, 3 μm, 4 μm, or 5 μm.
Preferably, step C adds a developer to perform development.
Preferably, the developer solution comprises a tetramethylammonium hydroxide solution.
In some embodiments of the present invention, the developer solution is typically, but not limited to, a tetramethylammonium hydroxide solution.
The concentration of the tetramethylammonium hydroxide solution was 2.38 wt%.
Embodiments of the present invention will be described in detail below with reference to examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention.
The specifications and types of the raw materials used in the examples and comparative examples of the present invention are shown in the following table 1, and those who do not indicate specific conditions are performed according to the conventional conditions or conditions suggested by the manufacturer.
TABLE 1 raw material specification and model table
Example 1
This example provides a negative photoresist composition, which is prepared by mixing 50g of 2000 molecular weight high silicone resin, 1g of methyl bischloromethyl triazine and 100g of propylene glycol methyl ether acetate, and filtering with a 0.2 μm pore size filter.
Example 2
This example provides a negative photoresist composition, which is prepared by mixing 50g of silicone resin with a molecular weight of 3000, 0.5g of naphthalimide triflate and 100g of propylene glycol methyl ether acetate, and filtering the mixture with a filter membrane with a pore size of 0.2 μm.
Example 3
This example provides a negative photoresist composition, which is prepared by mixing 50g of high-silicon resin with a molecular weight of 4000, 1g of p-methoxyphenyl acetonitrile p-toluenesulfonate and 100g of propylene glycol monomethyl ether acetate, and filtering the mixture with a filter membrane with a pore size of 0.2 μm.
Example 4
This example provides a negative photoresist composition, which is prepared by mixing 50g of high-silicon resin with molecular weight of 8000, 1g of methyl bischloromethyl triazine and 100g of propylene glycol methyl ether uniformly, and filtering with a filter membrane with pore size of 0.2 μm.
Example 5
This example provides a negative photoresist composition, which is different from example 3 in that the mass of the high-silicon resin is 800g, and the rest of the raw materials and methods are the same as those in example 3 and are not repeated herein.
Example 6
This example provides a negative photoresist composition, which is different from example 3 in that the mass of the high-silicon resin is 500g, and the rest of the raw materials and methods are the same as those in example 3 and are not repeated herein.
Example 7
This example provides a negative photoresist composition, which is different from example 3 in that the mass of p-methoxyphenylacetonitrile p-toluenesulfonate is 10g, and the other raw materials and methods are the same as those in example 3 and are not repeated herein.
Comparative example 1
The comparative example provides a negative photoresist composition, which is prepared by uniformly mixing 50g of contrast high-silicon resin with the molecular weight of 3000, 1g of methyl bischloromethyl triazine and 100g of propylene glycol methyl ether and filtering the mixture by using a filter membrane with the pore diameter of 0.2 mu m.
The structural formula of the comparative high-silicon resin is shown as follows:
comparative example 2
This comparative example provides a negative photoresist composition, which is different from example 3 in that the raw materials do not contain high silicon resin, the resin used is polyimide resin SUN-PAA136, and other raw materials and preparation methods are the same as those of example 3 and are not repeated herein.
Test example 1
The negative photoresist compositions provided in examples 1-7 and comparative examples 1-2 were spin-coated on the treated silicon wafers, respectively, and prebaked with a hot Plate (PAB) at a prebaking temperature of 100 ℃ for a prebaking time of 60 seconds while the rotation speed was adjusted so that the film thickness after drying was 3 μm. Passing through a mask plate, exposing by an exposure machine i-line, and measuring the exposure to 60mJ/cm2Baking (PEB) with a hot plate at 110 deg.C for 60 s. Soaking and developing the film for 60s by using 2.38 wt% of tetramethylammonium hydroxide solution (TMAH), cleaning the film by using deionized water, and hardening the film for 60s by using a hot plate at 110 ℃, thus completing the photoetching process, and recording the dielectric constant of the film in Table 2.
TABLE 2 dielectric constant data sheet
| Dielectric constant | |
| Example 1 | 3.0 |
| Example 2 | 2.9 |
| Example 3 | 2.8 |
| Example 4 | 3.0 |
| Example 5 | 2.7 |
| Example 6 | 2.7 |
| Example 7 | 3.1 |
| Comparative example 1 | 3.3 |
| Comparative example 2 | 3.3 |
As can be seen from Table 2, examples 1-7 each provided a negative photoresist composition having a dielectric constant less than 3.2 better than the negative photoresist compositions provided in comparative examples 1-2. The contrast ratio silicone resin used in comparative example 1 has a space network structure, and hydroxyl groups at two ends can undergo dehydration condensation reaction under acid catalysis, but the dielectric constant k cannot be reduced to below 3.2 due to low organic group content and difference in arrangement mode.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. A negative photoresist composition comprising a high silicon resin and a photosensitive acid generator.
2. The negative photoresist composition of claim 1, wherein the mass ratio of the high-silicon resin to the photosensitive acid generator is 10-70: 0.5-10.
3. The negative photoresist composition of claim 1, wherein the high-silicon resin has a formula of:
wherein n is an integer greater than 1;
preferably, the high silicone resin has a molecular weight of 1000-.
4. The negative photoresist composition of claim 1, wherein the photosensitive acid generator comprises a non-ionic acid generator;
preferably, the non-ionic acid generator comprises a triazine and/or a sulfonic acid compound.
5. The negative photoresist composition of claim 1, further comprising a solvent;
preferably, the solvent comprises an organic solvent;
preferably, the organic solvent includes at least one of propylene glycol methyl ether, propylene glycol propyl ether, propylene glycol methyl ether acetate, ethyl acetate and ethyl lactate.
6. The method of any of claims 1-5, wherein the high silicon resin, the photosensitive acid generator, and optionally a solvent are mixed uniformly.
7. Use of a negative photoresist composition according to any one of claims 1 to 5 or a negative photoresist composition prepared by the process of claim 6 in the manufacture of an integrated circuit.
8. A method of forming a photoresist pattern, the method comprising the steps of:
step A: spin-coating the negative photoresist composition according to any one of claims 1 to 5 or the negative photoresist composition prepared by the method of claim 6 on a substrate to form a photoresist layer;
and B: pre-baking the photoresist layer, and performing i-line exposure to obtain an exposed photoresist layer;
and C: and baking the exposed photoresist layer and developing to obtain the photoresist pattern.
9. The method of forming a photoresist pattern according to claim 8, wherein the temperature of the pre-baking is 90-110 ℃;
preferably, the pre-baking time is 30-90 s;
preferably, the temperature of the intermediate drying is 100-120 ℃;
preferably, the baking time is 30-90 s.
10. The method of forming a photoresist pattern according to claim 8, wherein the photoresist layer to be exposed is obtained in step B by pre-baking and before i-line exposure;
preferably, the film thickness of the photoresist layer to be exposed is 2-5 μm;
preferably, step C adds a developing solution for development;
preferably, the developer solution comprises a tetramethylammonium hydroxide solution.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103665381A (en) * | 2013-12-27 | 2014-03-26 | 蓝星化工新材料股份有限公司江西星火有机硅厂 | Synthesis method of hydroxyl capped polydimethylsiloxane |
| US20150322212A1 (en) * | 2012-12-19 | 2015-11-12 | Nissan Chemical Industries, Ltd. | Composition for forming silicon-containing resist underlayer film having cyclic diester group |
| CN107003613A (en) * | 2014-12-08 | 2017-08-01 | 日产化学工业株式会社 | Photoetching comprising the hydrolysable silanes with halogen-containing carboxylic acyloxy amido is with resist lower membrane formation composition |
| CN109563371A (en) * | 2016-08-29 | 2019-04-02 | 日产化学株式会社 | Polysiloxane composition comprising having carried out the silanol group of acetal protection |
| CN110809739A (en) * | 2017-07-06 | 2020-02-18 | 日产化学株式会社 | Composition for forming silicon-containing resist underlayer film, soluble in alkaline developer |
| CN113891906A (en) * | 2019-03-28 | 2022-01-04 | 日产化学株式会社 | Film-forming composition |
-
2021
- 2021-12-06 CN CN202111476489.6A patent/CN113985701A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150322212A1 (en) * | 2012-12-19 | 2015-11-12 | Nissan Chemical Industries, Ltd. | Composition for forming silicon-containing resist underlayer film having cyclic diester group |
| CN103665381A (en) * | 2013-12-27 | 2014-03-26 | 蓝星化工新材料股份有限公司江西星火有机硅厂 | Synthesis method of hydroxyl capped polydimethylsiloxane |
| CN107003613A (en) * | 2014-12-08 | 2017-08-01 | 日产化学工业株式会社 | Photoetching comprising the hydrolysable silanes with halogen-containing carboxylic acyloxy amido is with resist lower membrane formation composition |
| CN109563371A (en) * | 2016-08-29 | 2019-04-02 | 日产化学株式会社 | Polysiloxane composition comprising having carried out the silanol group of acetal protection |
| CN110809739A (en) * | 2017-07-06 | 2020-02-18 | 日产化学株式会社 | Composition for forming silicon-containing resist underlayer film, soluble in alkaline developer |
| CN113891906A (en) * | 2019-03-28 | 2022-01-04 | 日产化学株式会社 | Film-forming composition |
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