CN114133474B - High-precision resin for photoresist and preparation method thereof - Google Patents
High-precision resin for photoresist and preparation method thereof Download PDFInfo
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- CN114133474B CN114133474B CN202111391252.8A CN202111391252A CN114133474B CN 114133474 B CN114133474 B CN 114133474B CN 202111391252 A CN202111391252 A CN 202111391252A CN 114133474 B CN114133474 B CN 114133474B
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- 239000011347 resin Substances 0.000 title claims abstract description 37
- 229920005989 resin Polymers 0.000 title claims abstract description 37
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 27
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
- -1 amine compound Chemical class 0.000 claims abstract description 8
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims abstract description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 5
- 239000012986 chain transfer agent Substances 0.000 claims description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000009826 distribution Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- 229940116333 ethyl lactate Drugs 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 2
- 150000002978 peroxides Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000003573 thiols Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000002253 acid Substances 0.000 abstract description 10
- 238000009792 diffusion process Methods 0.000 abstract description 3
- 238000001259 photo etching Methods 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- FMEBJQQRPGHVOR-UHFFFAOYSA-N (1-ethylcyclopentyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(CC)CCCC1 FMEBJQQRPGHVOR-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention belongs to the technical field of photoresist, and particularly relates to high-precision resin for photoresist and a preparation method thereof. The resin for photoresist is prepared by adopting a compound (A), styrene, itaconate and methacrylate as polymerization monomers through free radical polymerization reaction; the compound (A) has the following structural formula:
Description
Technical Field
The invention belongs to the technical field of photoresist, and particularly relates to high-precision resin for photoresist and a preparation method thereof.
Background
Ultraviolet photoresists are mainly composed of resins, monomers, photosensitizers, and other additives, and under illumination, the photosensitizers are cleaved to generate active substances, which cause chemical reactions of the resins to change the properties of the resins, resulting in a change in the solubility of the resins in solvents or aqueous alkali, followed by development to produce patterns.
The resins of photoresists are mainly of two types, one is photoinitiated polymerization, and after photopolymerization, the resins are no longer dissolved in solvents or water to form crosslinked films, commonly referred to as negative photoresists; the other is that after illumination, the photosensitizer generates a strong acid, which causes structural changes of the resin, typically cleavage of ester bonds of the resin to generate acid, which changes the resin from oil-soluble to water-soluble, so that patterns can be produced, and such photoresists are called positive photoresists.
In the photoresist in the prior art, during the photo-acid generation process, the generated acid can be diffused to a non-exposure area during the diffusion process, and the problem of reduced pattern precision can be caused.
In view of this, the present invention has been made.
Disclosure of Invention
Aiming at the defect that photoetching precision is reduced due to the fact that a photo-acid generating part can be diffused to a non-exposure area in the prior art, the invention aims to provide the resin for the high-precision photoresist and the preparation method thereof.
The invention is realized by the following technical scheme:
the preparation method of the resin for the photoresist with high precision comprises the following steps of adopting a compound (A), itaconic acid ester and methacrylate as polymerization monomers, and preparing the resin for the photoresist through free radical polymerization reaction;
The compound (A) is an amine compound having at least one ethylenically unsaturated double bond.
Further, the free radical polymerization reaction is to dissolve a polymerization monomer in an organic solvent, and react for 2-480 min at a polymerization temperature of 50-120 ℃ through a thermal free radical initiator and a chain transfer agent.
Preferably, the molar fraction of styrene in the polymerized monomer is 0 to 0.6, the molar fraction of itaconate is 0 to 0.5, the molar fraction of methacrylate is 0 to 0.5, and the molar fraction of compound (a) is 0.05 to 0.5.
Preferably, the thermal free radical initiator is a peroxide or a diazo compound, and the amount of the thermal free radical initiator is 1 to 10 percent of the total mass of the polymerized monomers.
Preferably, the chain transfer agent is a thiol chain transfer agent, and the amount of the chain transfer agent is 0 to 5% of the total mass of the polymerized monomer.
Preferably, the organic solvent is one or more of ethylene glycol methyl ether, propylene glycol methyl ether, ethylene glycol methyl ether acetate, propylene glycol methyl ether acetate, ethyl lactate, butyl acetate and methyl amyl ketone.
Preferably, compound (a) has the following structural formula:
Wherein R 1 is H or methyl; r 2 is benzene ring or carbonyl; r 3 is O or N, and the number of R 3 is 0 or 1; r 4,R5 is independently selected from any one of H, methyl, ethyl and propyl; n is 0 to 5. Preferably, n=1.
Preferably, when R 2 is a benzene ring, the number of R 3 is 0 (i.e., R 3 can be absent).
The invention also provides a high-precision photoresist resin prepared by the method, which has the following structural formula:
Wherein, the structural general formula of R 6、R7、R8 is:
R 9 is H or CH 3, x=0 to 5.
Preferably, x=0 to 2.
Preferably, the weight average molecular weight of the resin is 3000 to 30000 and the molecular weight distribution index is 1.1 to 2.0.
Compared with the prior art, the invention has the beneficial effects that:
(1) The monomer used in the invention has low price, the performance can meet the application requirement of photoresist, the polymerization reaction is easy to control, and the prepared resin has good performance.
(2) In the prior art, acid generated by photoresist light can be diffused to a non-exposure area in the diffusion process, so that the pattern precision is reduced.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. The following description of at least one exemplary embodiment is merely exemplary in nature and is in no way intended to limit the invention, its application, or uses. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
According to the para-vinylaniline: 1-ethyl-cyclopentanol methacrylate: styrene molar ratio 0.2:0.3:0.5 g of monomer is weighed, 0.5 g of azodiisobutyronitrile is added according to the mass fraction of 5% of the monomer, 35 g of butyl acetate solvent is added, the mixture is stirred uniformly, nitrogen is filled for 15 minutes, and the mixture is heated to 100 ℃ while stirring for 3 hours to stop the reaction. The weight average molecular weight of the product resin was 1.6 ten thousand and the molecular weight distribution was 1.8 by GPC testing.
Example 2
According to dimethylaminoethyl acrylate: 1-ethyl-cyclopentanol methacrylate: styrene molar ratio 0.1:0.4:0.5 g of monomer was weighed and 0.5 g of azobisisobutyronitrile was added at 5% by mass of the monomer. 35 g of butyl acetate as a solvent, stirring uniformly, charging nitrogen in advance, discharging oxygen for 15 minutes, heating to 100 ℃ while stirring, then dropwise adding the monomer into a flask filled with the solvent at a flow rate of 1ml per minute, reacting for 2 hours after the dropwise adding is finished, and stopping the reaction. The weight average molecular weight of the product resin was 1.5 ten thousand and the molecular weight distribution was 1.6 by GPC testing.
Example 3
According to the method, the method comprises the following steps of: 1-ethyl-cyclopentanol methacrylate: styrene: mole ratio of itaconate 0.2:0.2:0.5:0.1 g of monomer is weighed, 0.7 g of azodiisobutyronitrile is added according to the mass fraction of 7 percent of the monomer, 35 g of ethyl lactate serving as a solvent is stirred uniformly, nitrogen is filled for 15 minutes, and the reaction is stopped after the mixture is heated to 120 ℃ for 2 hours while stirring. The weight average molecular weight of the product resin was 1.65 ten thousand and the molecular weight distribution was 1.8 by GPC testing.
Example 4
According to dimethylaminoethyl methacrylate: t-butyl methacrylate: styrene: mole ratio of itaconate 0.1:0.2:0.6:0.1 g of monomer is weighed, 0.7 g of azodiisobutyronitrile is added according to 7% of the mass fraction of the monomer, 0.5 g of chain transfer agent dodecyl mercaptan is added according to 5% of the mass fraction of the monomer, 35 g of solvent ethyl lactate is evenly stirred, nitrogen is filled for discharging oxygen for 15 minutes, and the reaction is stopped after the mixture is heated to 80 ℃ for 2.5 hours while stirring. The weight average molecular weight of the product resin was 1.6 ten thousand and the molecular weight distribution was 1.7 by GPC testing.
Example 5
According to the method, the method comprises the following steps of: t-butyl methacrylate: styrene: mole ratio of itaconate 0.3:0.2:0.3:0.2 g of monomer is weighed, 1.0 g of azodiisobutyronitrile is added according to 10 percent of the mass fraction of the monomer, 0.2 g of chain transfer agent dodecyl mercaptan is added according to 2 percent of the mass fraction of the monomer, 45 g of solvent ethylene glycol methyl ether is stirred uniformly, nitrogen is filled for discharging oxygen for 15 minutes, and the reaction is stopped after heating to 50 ℃ for 8 hours while stirring. The weight average molecular weight of the product resin was 1.8 ten thousand and the molecular weight distribution was 1.6 by GPC testing.
Test examples
The resins prepared in examples 1 to 5 were used as a base material, 1.85% of a photoacid generator (sulfonium salt) was added to prepare a 15% PGMEA solution, which was spin-coated at 2000 rpm, baked at 90 ℃ for 60 minutes and dried to a film thickness of 4 μm, and exposed to light at 100mJ/cm 2 for 120 seconds, then baked at 120 ℃ for 2 minutes, and developed with alkali water to prepare a photolithographic pattern. The resolution of the photoresist pattern was then measured using an electron scanning microscope, and the results are shown in table 1:
TABLE 1
| Test item | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 |
| Resolution ratio | 0.13 Micron | 0.17 Micrometer | 0.10 Micron | 0.14 Micron | 0.12 Micron |
Therefore, the embodiment of the invention utilizes the amine in the amine compound to absorb the acid generated by light, thereby avoiding the acid generated by light from diffusing to a non-exposure area, improving the high precision of the photoetching pattern and enabling the photoresist to have better resolution.
While the foregoing is directed to embodiments of the present invention, other and further details of the invention may be had by the present invention, it should be understood that the foregoing description is merely illustrative of the present invention and that no limitations are intended to the scope of the invention, except insofar as modifications, equivalents, improvements or modifications are within the spirit and principles of the invention.
Claims (8)
1. The preparation method of the resin for the photoresist is characterized in that the resin for the photoresist is prepared by adopting a compound (A), styrene, itaconate and methacrylate as polymerization monomers through free radical polymerization reaction;
the compound (A) is an amine compound having at least one ethylenically unsaturated double bond; the compound (A) has the following structural formula:
，
Wherein R 1 is H or methyl; r 2 is benzene ring or carbonyl; r 3 is O or N, and the number m of R 3 is 0 or 1; r 4,R5 is independently selected from any one of H, methyl, ethyl and propyl; n is 0 to 5;
The mole fraction of styrene in the polymerized monomer is 0.3-0.6, the mole fraction of itaconic acid ester is 0.1-0.5, the mole fraction of methacrylate is 0.2-0.5, and the mole fraction of compound (A) is 0.05-0.5.
2. The method for preparing a resin for a high-precision photoresist according to claim 1, wherein the radical polymerization is a reaction of dissolving a polymerization monomer in an organic solvent, and reacting for 2 to 480 minutes at a polymerization temperature of 50 to 120 ℃ by a thermal radical initiator and a chain transfer agent.
3. The method for preparing a resin for a high-precision photoresist according to claim 2, wherein the thermal radical initiator is a peroxide or a azo compound, and the amount of the thermal radical initiator is 1 to 10% of the total mass of the polymerized monomers.
4. The method for producing a resin for high-precision photoresists according to claim 2, wherein the chain transfer agent is a thiol chain transfer agent, and the amount of the chain transfer agent is 0 to 5% of the total mass of the polymerized monomers.
5. The method for producing a resin for high-precision photoresists according to claim 2, wherein the organic solvent is one or more of ethylene glycol methyl ether, propylene glycol methyl ether, ethylene glycol methyl ether acetate, propylene glycol methyl ether acetate, ethyl lactate, butyl acetate and methyl amyl ketone.
6. The method for producing a resin for high-precision photoresists according to claim 1, wherein R 2 is a benzene ring, and the number of R 3 is 0.
7. A high precision photoresist resin prepared according to any one of claims 1-6, having the following structural formula:
，
wherein, the structural general formula of R 6、R7、R8 is: ;
R 9 is H or CH 3, x=0 to 5.
8. The resin for high-precision photoresist according to claim 7, wherein x=0 to 2, the weight average molecular weight of the resin is 3000 to 30000, and the molecular weight distribution index is 1.1 to 2.0.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111391252.8A CN114133474B (en) | 2021-11-23 | 2021-11-23 | High-precision resin for photoresist and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111391252.8A CN114133474B (en) | 2021-11-23 | 2021-11-23 | High-precision resin for photoresist and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114133474A CN114133474A (en) | 2022-03-04 |
| CN114133474B true CN114133474B (en) | 2024-04-16 |
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| CN202111391252.8A Active CN114133474B (en) | 2021-11-23 | 2021-11-23 | High-precision resin for photoresist and preparation method thereof |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019244898A1 (en) * | 2018-06-22 | 2019-12-26 | 旭化成株式会社 | Photosensitive resin composition and resist pattern formation method |
| CN111205385A (en) * | 2020-02-28 | 2020-05-29 | 宁波南大光电材料有限公司 | Modified film-forming resin containing acid inhibitor, preparation method thereof and photoresist composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5836299B2 (en) * | 2012-08-20 | 2015-12-24 | 富士フイルム株式会社 | PATTERN FORMATION METHOD, ELECTRON-SENSITIVE OR EXTREME UV-SENSITIVE RESIN COMPOSITION, RESIST FILM, AND METHOD FOR PRODUCING ELECTRONIC DEVICE USING THEM |
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2021
- 2021-11-23 CN CN202111391252.8A patent/CN114133474B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019244898A1 (en) * | 2018-06-22 | 2019-12-26 | 旭化成株式会社 | Photosensitive resin composition and resist pattern formation method |
| CN111205385A (en) * | 2020-02-28 | 2020-05-29 | 宁波南大光电材料有限公司 | Modified film-forming resin containing acid inhibitor, preparation method thereof and photoresist composition |
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| CN114133474A (en) | 2022-03-04 |
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