CN115710328A - High molecular weight acrylic resin - Google Patents
High molecular weight acrylic resin Download PDFInfo
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- CN115710328A CN115710328A CN202211333216.0A CN202211333216A CN115710328A CN 115710328 A CN115710328 A CN 115710328A CN 202211333216 A CN202211333216 A CN 202211333216A CN 115710328 A CN115710328 A CN 115710328A
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- acrylic resin
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- 239000004925 Acrylic resin Substances 0.000 title claims abstract description 48
- 229920000178 Acrylic resin Polymers 0.000 title claims abstract description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 66
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims abstract description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000007787 solid Substances 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 238000010992 reflux Methods 0.000 claims abstract description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims abstract description 9
- 239000004342 Benzoyl peroxide Substances 0.000 claims abstract description 9
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims abstract description 9
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 9
- 235000019400 benzoyl peroxide Nutrition 0.000 claims abstract description 9
- WRAABIJFUKKEJQ-UHFFFAOYSA-N cyclopentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCC1 WRAABIJFUKKEJQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000000967 suction filtration Methods 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 230000009477 glass transition Effects 0.000 claims abstract description 3
- 239000007810 chemical reaction solvent Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 3
- 238000009826 distribution Methods 0.000 claims description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 31
- 239000011347 resin Substances 0.000 abstract description 15
- 229920005989 resin Polymers 0.000 abstract description 15
- 238000000034 method Methods 0.000 abstract description 12
- 238000004806 packaging method and process Methods 0.000 abstract description 5
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 description 14
- 238000000576 coating method Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 238000009713 electroplating Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000000178 monomer Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000009792 diffusion process Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000007747 plating Methods 0.000 description 5
- 229920003002 synthetic resin Polymers 0.000 description 5
- 239000000057 synthetic resin Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- -1 Methacrylic acid cyclopentanediol ester Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a high molecular weight acrylic resin, which is prepared by the following method: adding 5-5.2mol of dichloromethane into the flask, and introducing nitrogen for protection; adding styrene, isoprene, methacrylic acid, cyclopentyl methacrylate and hydroxyethyl methacrylate into a reaction flask according to a set molar ratio, and finally adding 0.01-0.03mol of catalyst benzoyl peroxide; heating the reaction to reflux, keeping the reflux state for 3 hours, and naturally cooling to normal temperature; the reaction in the flask was poured into a 1:4, stirring and separating out a solid, performing suction filtration, and dissolving in water with a mass ratio of 1:3, distilling under reduced pressure to obtain residual dichloromethane and water, and obtaining the acrylic resin solution. The invention is mainly used as the raw material of the negative photoresist in the advanced semiconductor packaging industry, the molecular weight of the resin is 5000-15000, the resin is distributed between 1.2-1.6, the content is more than 98 percent, the glass transition temperature is 120 ℃, and the viscosity is 20000-50000mPa.s.
Description
[ technical field ] A method for producing a semiconductor device
The invention relates to the technical field of photosensitive compositions, in particular to a high molecular weight acrylic resin.
[ background of the invention ]
The high-thick film negative photoresist used in the advanced packaging industry has high coating film thickness requirement which reaches more than 100um, and particularly needs to be developed in alkaline developing solution, soaked in acid electroplating solution and removed by alkaline degumming solution.
The viscosity of the positive photoresist for advanced packaging is within 1000mPa.s, the molecular weight is 6000-8000, the thickness of a single coating film is within 30um, even if double-layer coating is carried out, the upper limit of the film thickness can only reach 50um, because the positive photoresist photosensitizer absorbs a light source, if the film thickness is higher than 30um, the exposure dose needs to be increased, and simultaneously because the color of the positive photoresist is brick red, the positive photoresist is not transparent, light energy can be gradually absorbed in a thick film, the light energy is difficult to penetrate to the bottom, and the formed pattern is in a positive trapezoid shape.
Therefore, in order to meet the requirement of 110um thickness at the process end and ensure that the exposure can penetrate to the bottom, the acrylic negative photoresist is needed.
Another key node in the advanced packaging and electroplating process is electroplating resistance in electroplating solution, and because the requirement of the acid electroplating solution on materials is higher, the surface of the traditional positive photoresist is easy to crack after being electroplated due to high surface hardness and 45-degree use of the electroplating solution.
Therefore, it is necessary to provide a new high molecular weight acrylic resin to solve the above technical problems.
[ summary of the invention ]
The invention mainly aims to provide a high molecular weight acrylic resin, which realizes the coating of a photoresist with high film thickness at an application end by improving the molecular weight of the resin, improves the structure to solve the problem of toughness of a photoresist film layer so as to adapt to electroplating, and improves the purity of the resin to improve the resolution and stability of the photoresist.
The invention realizes the purpose through the following technical scheme: a high molecular weight acrylic resin prepared by the process of: adding 5-5.2mol of dichloromethane into a flask, introducing nitrogen for protection, and taking the dichloromethane as a reaction solvent without participating in the reaction; styrene, isoprene, methacrylic acid, cyclopentyl methacrylate and hydroxyethyl methacrylate are added into a reaction flask according to the mol ratio of 1 (1-1.1) to (1.2-1.3), and finally 0.01-0.03mol of catalyst benzoyl peroxide is added; heating the reaction to reflux, keeping the reflux state for 3 hours, and naturally cooling to normal temperature; the contents of the flask were poured into a 1:4, stirring to separate out a solid, performing suction filtration, and dissolving in water with a mass ratio of 1:3, distilling under reduced pressure to distill out residual dichloromethane and water to obtain an acrylic resin solution.
Dichloromethane is used as a reaction solvent, and mainly determines the initial concentration of the synthesis reaction, and further determines the reaction rate and the temperature rise, so that the synthesis efficiency is influenced. According to the invention, the optimum feeding proportion of styrene, isoprene, methacrylic acid, cyclopentyl methacrylate and hydroxyethyl methacrylate and the optimum catalyst input amount are adopted, so that the molecular weight and the conversion rate of the finally obtained product are ensured.
Furthermore, the molecular weight of the acrylic resin is 5000-15000, the distribution is 1.2-1.6, and the content of the acrylic resin in the acrylic resin solution is more than 98%.
Further, the glass transition temperature of the acrylic resin is 120 ℃, and the viscosity of the acrylic resin is 20000-50000mPa.s.
Further, the chemical structural formula of the acrylic resin is as follows:
compared with the prior art, the high molecular weight acrylic resin has the beneficial effects that: the heat resistance, plating resistance and rigidity of the acrylic resin are improved, and the photoresist prepared by adopting the acrylic resin has higher coating film thickness, resolution and stability and good toughness. In particular, the scheme mainly improves the photoresist of the copper electroplating process in advanced packaging,
1) The solid content of acrylic resin in the synthetic resin is controlled to be more than 98 percent, and the Tg value reaches 120 ℃, so that the toughness, heat-resistant characteristic and plating resistance of the resin are changed;
2) Meanwhile, the solid content of the acrylic resin in the synthetic resin is ensured to be more than 98 percent by matching with the components and the proportion of the synthetic acrylic resin;
3) Then, benzoyl peroxide is used as a catalyst, and the input amount of the benzoyl peroxide is controlled, so that the molecular weight of the synthesized acrylic resin is changed;
4) Finally, dichloromethane is used as a reaction solvent, the input amount of dichloromethane is strictly controlled, the viscosity of the acrylic resin after synthesis is changed, and the coating film thickness of the photoresist is improved under the comprehensive combination of the four points;
5) After the acrylic resin is prepared, the purification process is carried out, the purity of the acrylic resin is improved through the purification process, the resolution of the photoresist is improved, and the storage stability of the photoresist is guaranteed.
[ detailed description ] embodiments
Example 1:
this example is a high molecular weight acrylic resin prepared by the following method: adding 5mol of dichloromethane into a flask, introducing nitrogen for protection, and taking dichloromethane as a reaction solvent without participating in reaction; taking styrene, isoprene, methacrylic acid, cyclopentyl methacrylate and hydroxyethyl methacrylate, adding the styrene, isoprene, methacrylic acid, cyclopentyl methacrylate and hydroxyethyl methacrylate into a reaction flask according to a molar ratio of 1; heating the reaction to reflux, keeping the reflux state for 3 hours, and naturally cooling to normal temperature; the contents of the flask were poured into a 1:4, stirring to separate out a solid, performing suction filtration, and dissolving in water with a mass ratio of 1:3, distilling under reduced pressure to obtain residual dichloromethane and water, and obtaining the acrylic resin solution.
The invention changes the toughness and heat-resisting property of the resin by adjusting the Tg value and the solid content of the resin, and has the advantages of low Tg value, high resin rigidity and poor plating resistance property. The Tg value was varied by adjusting the synthesis ratio, the molecular weight was varied by the amount of catalyst used, the resin viscosity was adjusted by adjusting the amount of reaction solvent, and the coating film thickness of the photoresist was adjusted. The purity of the resin is adjusted through a purification process, after the resin reaches the proper purity, an initiator, a cross-linking agent, an additive and the like are added, and the target negative photoresist can be obtained through stirring, dissolving and filtering.
The more the catalyst is, the smaller the molecular weight is, the faster the developing rate of the prepared photoresist is, the film thickness of the photoresist with the same viscosity is reduced, and the coating rotating speed can be reduced at a client to improve the film thickness; when the molecular weight is too high, the solid content is reduced at the same viscosity, and the coating may produce gummy threads. Therefore, in this embodiment, the addition amount of the catalyst benzoyl peroxide is strictly controlled within a reasonable range, the molecular weight of the final synthetic resin is ensured, and not only can the rapid development efficiency be ensured, but also a certain coating film thickness can be ensured.
In the embodiment, under the condition that the molecular weight of the acrylic resin is certain, the viscosity is adjusted by adjusting the solid content of the resin, the reaction solvent is more during synthesis, the reaction activity of the synthesized resin is slow (the solid content is low during synthesis, the catalyst accounts for less in the solvent, the reaction is slow, the formed molecular weight is not large, and the conversion rate is low, so that the viscosity is low).
In the process of synthesizing the resin, the synthesis reaction generally cannot synthesize all the desired substances by 100 percent, and the monomers always remain, and the specific residual monomers and the content of the residual monomers are tested by a GC-MS instrument test, and then the purity of the synthetic resin can be improved by removing the specific monomers. In order to improve the synthesis efficiency, this example directly adopts a purification mode combining multiple modes, namely, "pour the reactants in the flask into 1:4, stirring and separating out a solid, performing suction filtration, and dissolving in water with a mass ratio of 1:3, distilling under reduced pressure to distill out residual dichloromethane and water, removing the monomers by utilizing the series of purification processes, further improving the purity of the product resin, being beneficial to improving the performance of finally preparing the photoresist, for example, the residual monomers influence the optical reaction of the photoresist, so that the photopolymerization degree of the photoresist is not enough, the residual monomers are easy to seep out of the photoresist during electroplating, the resolution ratio of the photoresist can also be influenced, and meanwhile, the storage stability of the photoresist can be influenced due to no polymerization of the residual monomers.
Example 2:
this example is a high molecular weight acrylic resin prepared by the following method: adding 5.1mol of dichloromethane into a flask, introducing nitrogen for protection, and taking dichloromethane as a reaction solvent without participating in reaction; taking styrene, isoprene, methacrylic acid, cyclopentyl methacrylate and hydroxyethyl methacrylate, and mixing the materials according to a molar ratio of 1:1.1:1:1.1, 1.3, adding into a reaction flask, and finally adding 0.01mol of catalyst benzoyl peroxide; heating the reaction to reflux, keeping the reflux state for 3 hours, and naturally cooling to normal temperature; the reaction in the flask was poured into a 1:4, stirring and separating out a solid, performing suction filtration, and dissolving in water with a mass ratio of 1:3, distilling under reduced pressure to distill out residual dichloromethane and water to obtain an acrylic resin solution.
Example 3:
this example is a high molecular weight acrylic resin prepared by the following method: adding 5.2mol of dichloromethane into a flask, introducing nitrogen for protection, and taking dichloromethane as a reaction solvent without participating in reaction; taking styrene, isoprene, methacrylic acid, cyclopentyl methacrylate and hydroxyethyl methacrylate, and mixing the materials according to a molar ratio of 1:1.1:1:1.1, 1.3, adding into a reaction flask, and finally adding 0.03mol of catalyst benzoyl peroxide; heating the reaction to reflux, keeping the reflux state for 3 hours, and naturally cooling to normal temperature; the contents of the flask were poured into a 1:4, stirring to separate out a solid, performing suction filtration, and dissolving in water with a mass ratio of 1:3, distilling under reduced pressure to obtain residual dichloromethane and water, and obtaining the acrylic resin solution.
In order to verify the effectiveness of the synthetic acrylic resin of the present invention, the present invention provides several comparative examples of the prepared acrylic resin, wherein the formula of the components and the process of the comparative examples are shown in table 1:
table 1 comparative examples acrylic resin synthesis ratios and processes
Components and Process | Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 |
Solvent/methylene chloride | 5mol | 5.1mol | 5.2mol | 7mol |
Styrene (meth) acrylic acid ester | 1mol | 1mol | 1mol | 1mol |
Isoprene (I) | 2mol | 1.1mol | 1.1mol | 1mol |
Methacrylic acid | 1mol | 1mol | 1mol | 1mol |
Methacrylic acid cyclopentanediol ester | 1.5mol | 1.1mol | 1.1mol | 1mol |
Hydroxyethyl methacrylate | 2mol | 1.3mol | 1.3mol | 1.2mol |
Catalyst/benzoyl peroxide | 0.02mol | 0.01mol | 0.05mol | 0.02mol |
Purification process | Is provided with | Is free of | Is provided with | Is free of |
In order to verify the effect of the invention, 20g of the acrylic resin prepared in the examples 1-3 and the comparative examples 1-4 were taken, 11g of the cross-linking agent and 3g of the photoinitiator were added to the acrylic resin, 0.04g of the leveling agent and 20g of propylene glycol methyl ether acetate were prepared into the photoresist, the photoresist was fully dissolved and filtered, the photoresist with the thickness of 110um was coated on the copper sheet, the pattern was obtained by prebaking at 120 ℃, after exposure, development was performed by 2.38% of the developing solution, the line width CD was measured, copper electroplating was performed, the development rate, the exposure energy, the CD size and the diffusion plating were observed, and the results are shown in table 2.
TABLE 2
Development time sec | Exposure mj/cm2 | CD(um) | Diffusion coating | |
Example 1 | 130 | 900 | 97.5 | OK |
Example 2 | 135 | 950 | 98.7 | OK |
Example 3 | 125 | 1000 | 97.8 | OK |
Comparative example 1 | 150 | 1200 | 98.2 | OK |
Comparative example 2 | 155 | 1100 | 100 | Diffusion coating |
Comparative example 3 | 170 | 1000 | 99 | Diffusion coating |
Comparative example 4 | 160 | 1300 | 99.2 | Diffusion coating |
For a negative photoresist with a thickness of 110um, which can penetrate to the bottom, the developing time is required to be within 150sec, the exposure energy is 1000 + -100 mj/cm2, the CD range is 98 + -1 um, and no diffusion plating is required. As shown in Table 2, the photoresists produced from the synthetic resins of examples 1-3 meet the above requirements.
What has been described above are merely some embodiments of the present invention. It will be apparent to those skilled in the art that various changes and modifications can be made without departing from the inventive concept thereof, and these changes and modifications can be made without departing from the spirit and scope of the invention.
Claims (4)
1. A high molecular weight acrylic resin characterized by: the preparation method comprises the following steps: adding 5-5.2mol of dichloromethane into a flask, introducing nitrogen for protection, and taking dichloromethane as a reaction solvent without participating in the reaction; adding styrene, isoprene, methacrylic acid, cyclopentyl methacrylate and hydroxyethyl methacrylate into a reaction flask according to the molar ratio of 1 (1-1.1) to (1.2-1.3), and finally adding 0.01-0.03mol of catalyst benzoyl peroxide; heating the reaction to reflux, keeping the reflux state for 3 hours, and naturally cooling to normal temperature; the reaction in the flask was poured into a 1:4, stirring to separate out a solid, performing suction filtration, dissolving in propylene glycol methyl ether acetate with the mass ratio of 1:3, performing reduced pressure distillation, and distilling out residual dichloromethane and water to obtain an acrylic resin solution.
2. The high molecular weight acrylic resin of claim 1, wherein: the molecular weight of the acrylic resin is 5000-15000, the distribution is 1.2-1.6, and the acrylic resin content in the acrylic resin solution is more than 98%.
3. The high molecular weight acrylic resin of claim 1, wherein: the glass transition temperature of the acrylic resin is 120 ℃, and the viscosity of the acrylic resin is 20000-50000mPa.s.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN116224716A (en) * | 2023-03-31 | 2023-06-06 | 苏州皓申智能科技有限公司 | Photoresist for preparing HJT solar cell copper grid and preparation method thereof |
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CN101517486A (en) * | 2006-11-10 | 2009-08-26 | 昭和高分子株式会社 | Photosensitive resin composition |
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CN114874381A (en) * | 2022-04-29 | 2022-08-09 | 江苏艾森半导体材料股份有限公司 | Alkali-soluble photosensitive negative photoresist resin |
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CN101517486A (en) * | 2006-11-10 | 2009-08-26 | 昭和高分子株式会社 | Photosensitive resin composition |
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Cited By (1)
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CN116224716A (en) * | 2023-03-31 | 2023-06-06 | 苏州皓申智能科技有限公司 | Photoresist for preparing HJT solar cell copper grid and preparation method thereof |
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