CN113354704A - Photoresist resin monomer synthesized by natural molecules and preparation method and application thereof - Google Patents
Photoresist resin monomer synthesized by natural molecules and preparation method and application thereof Download PDFInfo
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- CN113354704A CN113354704A CN202110700755.2A CN202110700755A CN113354704A CN 113354704 A CN113354704 A CN 113354704A CN 202110700755 A CN202110700755 A CN 202110700755A CN 113354704 A CN113354704 A CN 113354704A
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- resin monomer
- photoresist
- photoresist resin
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- natural molecules
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 62
- 239000011347 resin Substances 0.000 title claims abstract description 45
- 229920005989 resin Polymers 0.000 title claims abstract description 45
- 239000000178 monomer Substances 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 10
- -1 alicyclic hydrocarbon Chemical group 0.000 claims abstract description 10
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 150000002243 furanoses Chemical class 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims description 4
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 4
- 238000004090 dissolution Methods 0.000 abstract description 4
- 230000009471 action Effects 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000001259 photo etching Methods 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 description 1
- 229960000249 pregnenolone Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention relates to the technical field of photoresist, and discloses a photoresist resin monomer synthesized by natural molecules, a preparation method and application thereof, wherein the structural general formula of the photoresist resin monomer is as follows:
Description
Technical Field
The invention relates to the technical field of photoresist, in particular to a photoresist resin monomer synthesized by natural molecules and a preparation method and application thereof.
Background
The photolithography technique is a fine processing technique for transferring a pattern designed on a mask plate to a pattern on a substrate by using the chemical sensitivity of a photolithography material (particularly a photoresist) under the action of visible light, ultraviolet rays, electron beams and the like through the processes of exposure, development, etching and the like.
The main components of the photoresist material are resin, photoacid generator, and corresponding additives and solvents, and the material has chemical sensitivity with light (including visible light, ultraviolet light, electron beam, etc.) and changes its solubility in developer through photochemical reaction. According to the difference of photochemical reaction mechanism, the photoresist is divided into a positive photoresist and a negative photoresist: after exposure, the solubility of the photoresist in a developing solution is increased, and the photoresist with the same pattern as that of the mask is obtained and is called as a positive photoresist; after exposure, the photoresist has reduced solubility or even no solubility in a developing solution, and a negative photoresist with a pattern opposite to that of the mask is obtained.
In order to obtain a photoresist resin, we propose a photoresist resin monomer synthesized from natural molecules and a preparation method thereof.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a photoresist resin monomer synthesized by natural molecules, a preparation method and application thereof.
The invention provides the following technical scheme: a photoresist resin monomer synthesized by natural molecules, wherein the structural general formula of the photoresist resin monomer is as follows:
wherein R is hydrogen or alkyl, and M is alicyclic hydrocarbon.
Preferably, at least one of the following technical characteristics is also included:
a1) r is hydrogen or methyl;
a2) and M is alicyclic hydrocarbon of C3-C36.
Preferably, the photoresist resin monomer is selected from one of the following structures:
the preparation method of the photoresist resin monomer synthesized by natural molecules comprises the following synthesis steps:
wherein R is hydrogen or alkyl, and M is an alicyclic hydrocarbon;
the specific synthesis steps are as follows:
s1, preparation of intermediate II: carrying out an acetal reaction on the natural molecule I and furanose to form an intermediate II;
s2, preparation of photoresist resin monomer III: and carrying out esterification reaction on the intermediate II and acryloyl chloride or methacryloyl chloride or acrylic anhydride or methacrylic anhydride to generate a photoresist resin monomer III.
Preferably, the natural molecule i is selected from one of the following structures:
preferably, the natural molecule I and furanose react with each other through acetal reaction under the catalysis of hydrochloric acid to form an intermediate II.
The photoresist resin monomer synthesized from natural molecules is used for preparing photoresist.
Compared with the prior art, the photoresist resin monomer synthesized by natural molecules and the preparation method thereof have the following beneficial effects:
(1) according to the invention, the photoresist resin monomer contains an acetal structure, acid is generated by a photoacid generator group during exposure, and the ketal structure is broken under the action of acid, so that a polymerization main chain is broken, a small segment is formed, the edge roughness of a photoetching pattern can be improved, the resolution of the photoresist is improved, meanwhile, a hydroxyl group with good alkali solubility is formed, the dissolution in the developing process is facilitated, and the dissolution speed of the photoresist in a developing solution after exposure is increased;
(2) the photoresist resin monomer contains a furanose structure, so that the Critical Dimension Uniformity (CDU) and the Mask Error Factor (MEF) of a photoetching pattern can be improved;
(3) the invention has simple synthetic route and convenient operation.
Detailed Description
To make the objects, technical solutions and advantages of the embodiments of the present disclosure clearer and to describe more fully technical solutions of the embodiments of the present disclosure, and to keep the following description of the embodiments of the present disclosure clear and concise, detailed descriptions of known functions and known parts of the disclosure are omitted so as to avoid unnecessarily obscuring the concepts of the present disclosure.
A photoresist resin monomer synthesized by natural molecules, wherein the structural general formula of the photoresist resin monomer is as follows:
wherein R is hydrogen or alkyl, and M is alicyclic hydrocarbon.
At least one of the following technical characteristics is also included:
a1) r is hydrogen or methyl;
a2) and M is alicyclic hydrocarbon of C3-C36.
The photoresist resin monomer is selected from one of the following structures:
a method for preparing a photoresist resin monomer synthesized from natural molecules comprises the following synthesis steps:
wherein R is hydrogen or alkyl, and M is an alicyclic hydrocarbon;
the specific synthesis steps are as follows:
s1, preparation of intermediate II: carrying out an acetal reaction on the natural molecule I and furanose to form an intermediate II;
s2, preparation of photoresist resin monomer III: and carrying out esterification reaction on the intermediate II and acryloyl chloride or methacryloyl chloride or acrylic anhydride or methacrylic anhydride to generate a photoresist resin monomer III.
Example 1
The preparation of the photoresist resin monomer 1-3 comprises the following synthetic route:
the synthesis steps are as follows:
preparation of intermediates 1-2: furanose (2g, 13.3mmol), pregnenolone 1-1(5g, 15.8mmol) and hydrochloric acid (0.25g, 6.9mmol) were added to a methanol solution (50g) and stirred at 25 ℃ for 8 h. Ethyl acetate (100g) and 10% aqueous potassium carbonate (20g) were then added, stirred for 30 minutes, and allowed to stand to give an organic layer. The obtained organic layer was washed three times with deionized water, dried and concentrated to give a crude product, which was purified by column chromatography to give intermediate 1-2(3.8g, 8.21mmol, 61.7%).
Preparation of Photoresist resin monomers 1-3: intermediate 1-2(3.8g, 8.21mmol), pyridine (1.6g, 20.2mmol) and 4-dimethylaminopyridine (0.1g, 0.82mmol) were dissolved in tetrahydrofuran (40g) and methacrylic anhydride (2.8g, 18.2mmol) was added and stirred for 2 hours. Ethyl acetate (50g) and a 5% aqueous solution of oxalic acid (10g) were then added, stirred for 30 minutes, and allowed to stand to obtain an organic layer. The obtained organic layer was added with 10% potassium carbonate aqueous solution (5g), followed by washing with deionized water 3 times, and the organic layer was concentrated to obtain resin monomers 1 to 3(4.5g, 7.52mmol, 91.5%).
Example 2
The preparation of the photoresist resin monomer 2-3 comprises the following synthetic route:
the synthesis steps are as follows:
preparation of intermediate 2-2: furanose (0.5g, 3.33mmol), 17-hydroxy-3-kauri-one 2-1(1g, 3.28mmol) and hydrochloric acid (0.07g, 1.94mmol) were added to a methanol solution (10g) and stirred at 25 ℃ for 2 hours. Ethyl acetate (20g) and 10% aqueous potassium carbonate (5g) were then added to the solution, and the mixture was allowed to stand to obtain an organic layer. The obtained organic layer was washed three times with deionized water, dried and concentrated to give a crude product, which was purified by column chromatography to give intermediate 2-2(0.8g, 1.78mmol, 53.3%).
Preparation of photoresist resin monomer 2-3: intermediate 2-2(0.8g, 1.78mmol), pyridine (0.35g, 4.42mmol) and 4-dimethylaminopyridine (0.02g, 0.16mmol) were dissolved in tetrahydrofuran (10g) and methacryloyl chloride (0.42g, 0.40mmol) was added and stirred for 2 hours. Ethyl acetate (20g) and a 5% aqueous solution of oxalic acid (2g) were then added, stirred for 30 minutes, and allowed to stand to obtain an organic layer. The resulting organic layer was added with 10% aqueous potassium carbonate solution (1g), followed by washing with deionized water 3 times, and the organic layer was concentrated to give photoresist resin monomers 2-3(0.9g, 1.53mmol, 86.4%).
Example 3
The preparation of the photoresist resin monomer 3-3 comprises the following synthetic route:
the synthesis steps are as follows:
preparation of intermediate 3-2: furanose (0.3g, 2mmol), friedelin-3-one 29-hydroxy 3-1(1g, 2.19mmol) and hydrochloric acid (0.04g, 1.11mmol) were added to a methanol solution (10g), and the mixture was stirred at 25 ℃ for 8 hours. Ethyl acetate (20g) and 10% aqueous potassium carbonate (5g) were then added to the solution, and the mixture was allowed to stand to obtain an organic layer. The obtained organic layer was washed three times with deionized water, dried and concentrated to give a crude product, which was purified by column chromatography to give intermediate 3-2(0.75g, 1.24mmol, 62.3%).
Preparation of photoresist resin monomer 3-3: intermediate 3-2(0.75g, 1.24mmol), pyridine (0.3g, 3.8mmol) and 4-dimethylaminopyridine (0.02g, 0.16mmol) were dissolved in tetrahydrofuran (10g) and methacrylic anhydride (0.4g, 2.59mmol) was added and stirred for 2 hours. Ethyl acetate (20g) and a 5% aqueous solution of oxalic acid (2g) were then added to the solution, and the mixture was allowed to stand to obtain an organic layer. The resulting organic layer was added with 10% aqueous potassium carbonate solution (2g), followed by washing with deionized water 3 times, and the organic layer was concentrated to give photoresist resin monomer 3-3(0.85g, 1.15mmol, 92.5%).
The above embodiments are only exemplary embodiments of the present invention, and are not intended to limit the present invention, and the scope of the present invention is defined by the claims. Various modifications and equivalents may be made by those skilled in the art within the spirit and scope of the present invention, and such modifications and equivalents should also be considered as falling within the scope of the present invention.
Claims (7)
1. A photoresist resin monomer synthesized by natural molecules is characterized in that the structural general formula of the photoresist resin monomer is as follows:
wherein R is hydrogen or alkyl, and M is alicyclic hydrocarbon.
2. The photoresist resin monomer synthesized from natural molecules according to claim 1, further comprising at least one of the following technical features:
a1) r is hydrogen or methyl;
a2) and M is alicyclic hydrocarbon of C3-C36.
3. The photoresist resin monomer synthesized from natural molecules according to claim 1, wherein the photoresist resin monomer is selected from one of the following structures:
4. the method for preparing a photoresist resin monomer synthesized from natural molecules according to any one of claims 1 to 3, comprising the following synthetic steps:
wherein R is hydrogen or alkyl, and M is an alicyclic hydrocarbon;
the specific synthesis steps are as follows:
s1, preparation of intermediate II: carrying out an acetal reaction on the natural molecule I and furanose to form an intermediate II;
s2, preparation of photoresist resin monomer III: and carrying out esterification reaction on the intermediate II and acryloyl chloride or methacryloyl chloride or acrylic anhydride or methacrylic anhydride to generate a photoresist resin monomer III.
5. The method of claim 4, wherein the natural molecule I is selected from one of the following structures:
6. the method for preparing a monomer for a photoresist resin synthesized from natural molecules as claimed in claim 4, wherein the specific preparation steps of the intermediate II in S1 are as follows: the natural molecule I and furanose react with acetal under the catalysis of hydrochloric acid to form an intermediate II.
7. A photoresist resin monomer synthesized from natural molecules according to any one of claims 1 to 3 for use in the preparation of a photoresist.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110700755.2A CN113354704A (en) | 2021-06-24 | 2021-06-24 | Photoresist resin monomer synthesized by natural molecules and preparation method and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110700755.2A CN113354704A (en) | 2021-06-24 | 2021-06-24 | Photoresist resin monomer synthesized by natural molecules and preparation method and application thereof |
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| Publication Number | Publication Date |
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| CN113354704A true CN113354704A (en) | 2021-09-07 |
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| CN202110700755.2A Pending CN113354704A (en) | 2021-06-24 | 2021-06-24 | Photoresist resin monomer synthesized by natural molecules and preparation method and application thereof |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201804249A (en) * | 2016-05-13 | 2018-02-01 | 住友化學股份有限公司 | Photoresist composition |
| CN111116605A (en) * | 2019-12-28 | 2020-05-08 | 上海博栋化学科技有限公司 | Photoresist resin monomer synthesized from aldopentose and synthesis method thereof |
-
2021
- 2021-06-24 CN CN202110700755.2A patent/CN113354704A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201804249A (en) * | 2016-05-13 | 2018-02-01 | 住友化學股份有限公司 | Photoresist composition |
| CN111116605A (en) * | 2019-12-28 | 2020-05-08 | 上海博栋化学科技有限公司 | Photoresist resin monomer synthesized from aldopentose and synthesis method thereof |
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Application publication date: 20210907 |