CN117471852A - Inkjet type nano-imprinting adhesive for semiconductor manufacturing and preparation method thereof - Google Patents
Inkjet type nano-imprinting adhesive for semiconductor manufacturing and preparation method thereof Download PDFInfo
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- CN117471852A CN117471852A CN202311448204.7A CN202311448204A CN117471852A CN 117471852 A CN117471852 A CN 117471852A CN 202311448204 A CN202311448204 A CN 202311448204A CN 117471852 A CN117471852 A CN 117471852A
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- functional monomer
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- 239000000853 adhesive Substances 0.000 title claims abstract description 32
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 239000004065 semiconductor Substances 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000000178 monomer Substances 0.000 claims abstract description 54
- 239000003085 diluting agent Substances 0.000 claims abstract description 35
- 239000003292 glue Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 230000003749 cleanliness Effects 0.000 claims abstract description 4
- 239000012535 impurity Substances 0.000 claims abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000004814 polyurethane Substances 0.000 claims description 9
- 229920002635 polyurethane Polymers 0.000 claims description 9
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 8
- RDLGTRBJUAWSAF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-2-one Chemical compound CC(=O)CC1C=CC=CC1(C)O RDLGTRBJUAWSAF-UHFFFAOYSA-N 0.000 claims description 7
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 7
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 claims description 7
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 7
- 238000005303 weighing Methods 0.000 claims description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 5
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical class C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 5
- 239000013067 intermediate product Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000032683 aging Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000000630 rising effect Effects 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 6
- -1 acrylic ester Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000001127 nanoimprint lithography Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000012795 verification Methods 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
-
- 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)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention discloses an inkjet type nano imprinting adhesive for semiconductor manufacture, which consists of a functional oligomer, a functional monomer, a photoinitiator and a diluent; the viscosity range of the inkjet type nano imprinting adhesive is 5-50 cP; the surface energy of the inkjet nano imprinting glue is 25-45 mN/m; the cleanliness of the ink-jet nano imprinting adhesive is less than 220nm, and the content of impurities is less than 1ppm; and the curing time of the inkjet type nano imprinting adhesive is less than or equal to 1min. The viscosity of the nano imprinting glue is regulated by adding a diluent, so that the viscosity range is within 5-50 cP; the functional oligomer and the functional monomer are matched to change the surface energy, the functional monomer is introduced when the surface energy is low, the functional monomer and the functional oligomer have excellent compatibility, and the functional monomer contains polar functional groups such as hydroxyl, carboxyl and the like; the surface energy is high, and the surface energy is reduced through the combination of an aromatic ring and a long carbon chain; the obtained nano imprinting glue has the surface energy of 25-45 mN/m, and the low viscosity and the proper surface energy are controlled, so that the nano imprinting glue can be used for ink jet.
Description
Technical Field
The invention relates to the technical field of nanoimprint lithography, in particular to an inkjet nanoimprint lithography adhesive for semiconductor manufacturing and a preparation method thereof.
Background
The nano imprinting glue material, the imprinting template, the imprinting equipment and the imprinting process are core elements of the nano imprinting technology, wherein the nano imprinting glue has the function equivalent to the photoresist function in the photoetching technology, and is an indispensable material foundation and guarantee in the implementation process of the nano imprinting technology. The characteristics of nanoimprint resist are one of the key factors affecting resolution, fidelity, and pattern etch transfer of the imprint pattern. Along with the continuous development and promotion of the nanoimprint technology, the nanoimprint technology touches the field of semiconductor manufacturing, the requirements on nanoimprint glue are higher and higher, the nanoimprint glue is more and more subdivided, and common coating type nanoimprint glue (dip coating, spin coating, slit coating, blade knife coating and bar graph) cannot meet the field of semiconductor manufacturing, because fixed-point glue feeding is required as required; however, inkjet type imprint gels are required to satisfy low viscosity and suitable surface energy. Therefore, development of a higher quality nanoimprint resist system, particularly an inkjet nanoimprint resist material suitable for a step nanoimprint process of semiconductor manufacturing, is a key material guarantee for realizing the nanoimprint technology facing the semiconductor manufacturing.
Disclosure of Invention
The invention aims to provide an inkjet type nano imprinting adhesive for semiconductor manufacturing and a preparation method thereof, which are used for overcoming the defects in the prior art.
In order to achieve the above purpose, the present invention provides the following technical solutions:
the application discloses an inkjet type nano imprinting adhesive for semiconductor manufacturing, which consists of a functional oligomer, a functional monomer, a photoinitiator and a diluent; the functional oligomer, the functional monomer and the diluent are prepared from the following components in parts by mass: 5-15 parts of functional oligomer, 1-3 parts of functional monomer and 82-94 parts of diluent; the dosage of the photoinitiator is 1-2% of the sum of the functional oligomer and the functional monomer; the viscosity range of the inkjet type nano imprinting adhesive is 5-50 cP; the surface energy of the inkjet nano imprinting glue is 25-45 mN/m; the cleanliness of the ink-jet nano imprinting adhesive is less than 220nm, and the content of impurities is less than 1ppm; and the curing time of the inkjet type nano imprinting adhesive is less than or equal to 1min.
Preferably, the functional oligomer is one or more of aromatic polyurethane acrylate, modified epoxy acrylate and acrylate mixture.
Preferably, the functional monomer is one or more of trimethylolpropane trimethacrylate and dipentaerythritol acrylate.
Preferably, the photoinitiator is one or more of 1-hydroxy cyclohexyl phenyl ketone and 2-hydroxy-2-methyl phenyl acetone.
Preferably, the diluent is one or more of isopropanol, hydroxyethyl acrylate and cyclohexanone.
The invention also discloses a preparation method of the inkjet type nano imprinting adhesive for semiconductor manufacturing, which comprises the following steps:
s1, weighing a diluent and an initiator, and placing the diluent and the initiator in a water bath at 4-7 ℃ to obtain a primary product;
s2, weighing a functional monomer, adding the functional monomer into the primary product of the S1, and stirring for 40-60 min; obtaining an intermediate product;
s3, weighing the functional oligomer, adding the functional oligomer into the intermediate product of the S2, and stirring for 20-40 min; obtaining a preliminary nano-imprinting adhesive;
and S4, heating the temperature to room temperature, and aging for 5-7 hours to obtain the inkjet type nano imprinting adhesive.
Wherein, the functional oligomer, the functional monomer and the diluent are in parts by mass: 5-15 parts of functional oligomer, 1-3 parts of functional monomer and 82-94 parts of diluent; the dosage of the photoinitiator is 1-2% of the sum of the functional oligomer and the functional monomer.
Preferably, steps S1 to S4 are all performed under a shading condition.
Preferably, in the step S4, the temperature rising rate of the temperature is 4-6 min/DEG C.
Preferably, the ink-jet effect test of the ink-jet type imprinting glue comprises the following conditions: inkjet drop volume, inkjet speed: the ink jet droplet volume is 3-10 pL, and the ink jet speed is 6 m/s.
Preferably, the verification of the impression result of the ink-jet type impression compound comprises the following conditions: macrostructure, microstructure, mechanical strength, cure shrinkage: the imprinting macroscopic result of the ink-jet type imprinting adhesive is required to be consistent with that of an original model, the precision error of a microstructure is less than 1%, the mechanical strength of the ink-jet type imprinting adhesive is greater than 60 MPa, and the solidification shrinkage rate of the ink-jet type imprinting adhesive is less than 5%.
The invention has the beneficial effects that:
1. according to the invention, the viscosity of the nano imprinting glue is regulated by adding the diluent, so that the viscosity range is within 5-50 cP; the functional oligomer and the functional monomer are matched to change the surface energy, and the functional monomer is introduced when the surface energy is low, so that the functional monomer and the functional oligomer have excellent compatibility, and the functional monomer contains polar functional groups such as hydroxyl, carboxyl and the like; the surface energy is high, and the surface energy is reduced through the combination of an aromatic ring and a long carbon chain; the obtained nano imprinting glue has the surface energy of 25-45 mN/m, and the low viscosity and the proper surface energy are controlled, so that the nano imprinting glue can be used for ink jet;
2. mechanical properties of nanoimprint resist: the crosslinking density is improved by introducing an aromatic ring, epoxy and other annular structures and improving the functionality, so that the mechanical properties are improved.
3. An initiator with high initiation efficiency is adopted, and a strategy of compounding multiple initiators is adopted, so that the curing rate is improved.
The features and advantages of the present invention will be described in detail by way of example with reference to the accompanying drawings.
Drawings
FIG. 1 shows the spray result of spray type impression compound;
FIG. 2 shows the imprint results of a spray-type imprint resist;
fig. 3 microscopic results of spray-on imprint resist.
Detailed Description
The present invention will be further described in detail with reference to the drawings and examples, in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the detailed description and specific examples, while indicating the invention, are intended for purposes of illustration only and are not intended to limit the scope of the invention. In addition, in the following description, descriptions of well-known structures and techniques are omitted so as not to unnecessarily obscure the present invention.
The invention relates to an inkjet nano-imprinting adhesive for semiconductor manufacture, which consists of a functional oligomer, a functional monomer, a photoinitiator and a diluent; the functional oligomer, the functional monomer and the diluent are prepared from the following components in parts by mass: 5-15 parts of functional oligomer, 1-3 parts of functional monomer and 82-94 parts of diluent; the dosage of the photoinitiator is 1-2% of the sum of the functional oligomer and the functional monomer; the viscosity range of the inkjet type nano imprinting adhesive is 5-50 cP; the surface energy of the inkjet nano imprinting glue is 25-45 mN/m; the cleanliness of the ink-jet nano imprinting adhesive is less than 220nm, and the content of impurities is less than 1ppm; and the curing time of the inkjet type nano imprinting adhesive is less than or equal to 1min.
Wherein the functional oligomer is one or more of aromatic polyurethane acrylate, modified epoxy acrylate and acrylate mixture; the functional monomer is one or more of trimethylolpropane trimethacrylate and dipentaerythritol acrylate; the photoinitiator is one or more of 1-hydroxy cyclohexyl phenyl ketone and 2-hydroxy-2-methyl phenyl acetone; the diluent is one or more of isopropanol, hydroxyethyl acrylate and cyclohexanone.
Example 1
In the embodiment, 10 parts of functional oligomer, 2 parts of functional monomer and 88 parts of diluent are adopted; the dosage of the photoinitiator is 2% of the sum of the functional oligomer and the functional monomer; specifically, the functional oligomer is aromatic polyurethane acrylate; the functional monomer is trimethylolpropane trimethacrylate; the initiator is 1-hydroxy cyclohexyl phenyl ketone; the diluent is prepared from isopropanol;
the performance of this example is as follows: viscosity 27 cP, surface energy 25 mN/m, high curing speed 30s and high water resistance;
example 2
In the embodiment, 5 parts of functional oligomer, 1 part of functional monomer and 94 parts of diluent are adopted; the dosage of the photoinitiator is 1% of the sum of the functional oligomer and the functional monomer; specifically, the functional oligomer is a mixture of modified epoxy acrylate and acrylic ester (1:1); the functional monomer is dipentaerythritol acrylic ester; the initiator is 2-hydroxy-2-methyl phenyl acetone; the diluent is prepared from cyclohexanone;
the performance of this example is as follows: viscosity 10 cP, surface energy 37 mN/m, high curing speed 40s, low viscosity and good film forming property.
Example 3
In the embodiment, 14 parts of functional oligomer, 2 parts of functional monomer and 82 parts of diluent are adopted; the dosage of the photoinitiator is 2% of the sum of the functional oligomer and the functional monomer; specifically, the functional oligomer is an aromatic polyurethane acrylate and acrylate mixture (the aromatic polyurethane acrylate and acrylate mixture respectively account for 7 percent); the functional monomer is selected from trimethylolpropane trimethacrylate and dipentaerythritol acrylate (each station of the trimethylolpropane trimethacrylate and the dipentaerythritol acrylate is 1 percent); the initiator is selected from 1-hydroxy cyclohexyl phenyl ketone and 2-hydroxy-2-methyl phenyl acetone (1:1); the diluent is prepared from hydroxyethyl acrylate;
the performance of this example is as follows: viscosity 43 cP, surface energy 43 mN/m, high curing speed 20s and high strength.
Comparative example 1:
in the embodiment, 10 parts of functional oligomer and 90 parts of diluent are adopted; the dosage of the photoinitiator is 2% of the mass of the functional oligomer; specifically, the functional oligomer is aromatic polyurethane acrylate; the initiator is 1-hydroxy cyclohexyl phenyl ketone; the diluent is prepared from isopropanol;
the performance of this example is as follows: viscosity 29 cP, surface energy 18 mN/m; ink jet cannot be performed;
comparative example 2:
in the embodiment, 5 parts of functional oligomer, 5 parts of functional monomer and 90 parts of diluent are adopted; the dosage of the photoinitiator is 1% of the sum of the functional oligomer and the functional monomer; specifically, the functional oligomer is a mixture of modified epoxy acrylate and acrylic ester (1:1); the functional monomer is dipentaerythritol acrylic ester; the initiator is 2-hydroxy-2-methyl phenyl acetone; the diluent is prepared from cyclohexanone;
the performance of this example is as follows: viscosity 10 cP, surface energy 54 mN/m; ink jet tailing;
comparative example 3:
in the embodiment, 14 parts of functional oligomer, 4 parts of functional monomer and 82 parts of diluent are adopted; the dosage of the photoinitiator is 2% of the sum of the functional oligomer and the functional monomer; specifically, the functional oligomer is an aromatic polyurethane acrylate and acrylate mixture (the aromatic polyurethane acrylate and acrylate mixture respectively account for 7 percent); the functional monomer is selected from trimethylolpropane trimethacrylate and dipentaerythritol acrylate (each station of the trimethylolpropane trimethacrylate and dipentaerythritol acrylate is 2 percent); the initiator is selected from 1-hydroxy cyclohexyl phenyl ketone and 2-hydroxy-2-methyl phenyl acetone (1:1); the diluent is prepared from hydroxyethyl acrylate;
the performance of this example is as follows: viscosity 43 cP, surface energy 57 mN/m, inkjet tail, with planetary droplets;
referring to fig. 1, the inkjet nanoimprint resist obtained in example 1 is sprayed, droplets are uniformly distributed, and the resist can be fed according to the requirements of the nanoimprint template, which is hardly comparable with spin-coating, and spin coating can only cover the whole surface;
referring to fig. 2, the inkjet nanoimprint resist obtained in example 1 was subjected to inkjet and imprinting, and compared with general spin coating, the structure region could be customized privately;
referring to fig. 3, in order to show the microstructure of the inkjet type nanoimprint resist of example 1, the prepared resist may be used for nanoimprint by inkjet.
As can be seen from a comparison of example 1 with comparative example 1, the addition of the reactive monomer increases the surface energy; so that the prepared ink-jet nano imprinting adhesive can perform effective ink jet;
as can be seen from a comparison of example 2 with comparative example 2, the addition of reactive monomers increases the surface energy; however, excessive addition of the active monomer can cause tailing when the prepared ink-jet nano imprinting adhesive is used for ink jet;
as can be seen from a comparison of example 3 with comparative example 3, the addition of reactive monomers increases the surface energy; however, excessive addition of the active monomer can cause tailing when the prepared ink-jet type nano imprinting adhesive is used for ink jet, and even liquid drops can occur along with higher surface energy.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, or alternatives falling within the spirit and principles of the invention.
Claims (8)
1. An inkjet nano-imprinting adhesive for semiconductor manufacturing is characterized in that: the functional oligomer consists of functional oligomer, functional monomer, photoinitiator and diluent; the functional oligomer, the functional monomer and the diluent are prepared from the following components in parts by mass: 5-15 parts of functional oligomer, 1-3 parts of functional monomer and 82-94 parts of diluent; the dosage of the photoinitiator is 1-2% of the sum of the functional oligomer and the functional monomer; the viscosity range of the inkjet type nano imprinting adhesive is 5-50 cP; the surface energy of the inkjet nano imprinting glue is 25-45 mN/m; the cleanliness of the ink-jet nano imprinting adhesive is less than 220nm, and the content of impurities is less than 1ppm; and the curing time of the inkjet type nano imprinting adhesive is less than or equal to 1min.
2. The inkjet nanoimprint resist of claim 1, wherein the functional oligomer is one or more of aromatic polyurethane acrylate, modified epoxy acrylate, and acrylate mixture.
3. The inkjet nanoimprint resist of claim 1, wherein the functional monomer is one or more of trimethylolpropane trimethacrylate and dipentaerythritol acrylate.
4. An inkjet nanoimprint resist for semiconductor fabrication according to claim 1, wherein the photoinitiator is one or more of 1-hydroxycyclohexyl phenyl ketone and 2-hydroxy-2-methylphenyl acetone.
5. The inkjet nanoimprint resist for semiconductor manufacturing according to claim 1, wherein the diluent is one or more of isopropanol, hydroxyethyl acrylate, and cyclohexanone.
6. The preparation method of the inkjet nano-imprinting adhesive for semiconductor manufacturing is characterized by comprising the following steps of: the method comprises the following steps:
s1, weighing a diluent and an initiator, and placing the diluent and the initiator in a water bath at 4-7 ℃ to obtain a primary product;
s2, weighing a functional monomer, adding the functional monomer into the primary product of the S1, and stirring for 40-60 min; obtaining an intermediate product;
s3, weighing the functional oligomer, adding the functional oligomer into the intermediate product of the S2, and stirring for 20-40 min; obtaining a preliminary nano-imprinting adhesive;
s4, heating the temperature to room temperature, and aging for 5-7 hours to obtain the inkjet nano imprinting adhesive;
wherein, the functional oligomer, the functional monomer and the diluent are in parts by mass: 5-15 parts of functional oligomer, 1-3 parts of functional monomer and 82-94 parts of diluent; the dosage of the photoinitiator is 1-2% of the sum of the functional oligomer and the functional monomer.
7. The method for preparing the inkjet nano-imprinting glue for semiconductor manufacturing according to claim 6, wherein the method comprises the following steps: the steps S1 to S4 are all carried out under the shading condition.
8. The method for preparing the inkjet nano-imprinting glue for semiconductor manufacturing according to claim 6, wherein the method comprises the following steps: in the step S4, the temperature rising rate of the temperature is 4-6 min/DEG C.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311448204.7A CN117471852B (en) | 2023-11-02 | 2023-11-02 | Inkjet type nano-imprinting adhesive for semiconductor manufacturing and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311448204.7A CN117471852B (en) | 2023-11-02 | 2023-11-02 | Inkjet type nano-imprinting adhesive for semiconductor manufacturing and preparation method thereof |
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| CN117471852B CN117471852B (en) | 2024-05-14 |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101706638A (en) * | 2009-10-23 | 2010-05-12 | 上海市纳米科技与产业发展促进中心 | Ultraviolet nanoimprint resist and components thereof |
| JP2012134446A (en) * | 2010-11-30 | 2012-07-12 | Jnc Corp | Curable composition for optical nanoimprint and hardened film obtained from curable composition |
| CN103279011A (en) * | 2013-06-14 | 2013-09-04 | 中国科学院光电技术研究所 | Thiol-ene ultraviolet light curing nano imprinting material |
| WO2017101465A1 (en) * | 2015-12-15 | 2017-06-22 | 南方科技大学 | Nanoimprinted photoresist and preparation method therefor |
| US20190056663A1 (en) * | 2015-05-26 | 2019-02-21 | South University Of Science And Technology Of China | Expansion polymerization imprinting glue for nano-printing |
| CN116478650A (en) * | 2023-04-27 | 2023-07-25 | 江苏斯迪克新材料科技股份有限公司 | Normal-temperature high-modulus ultraviolet impression compound and preparation method thereof |
-
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- 2023-11-02 CN CN202311448204.7A patent/CN117471852B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101706638A (en) * | 2009-10-23 | 2010-05-12 | 上海市纳米科技与产业发展促进中心 | Ultraviolet nanoimprint resist and components thereof |
| JP2012134446A (en) * | 2010-11-30 | 2012-07-12 | Jnc Corp | Curable composition for optical nanoimprint and hardened film obtained from curable composition |
| CN103279011A (en) * | 2013-06-14 | 2013-09-04 | 中国科学院光电技术研究所 | Thiol-ene ultraviolet light curing nano imprinting material |
| US20190056663A1 (en) * | 2015-05-26 | 2019-02-21 | South University Of Science And Technology Of China | Expansion polymerization imprinting glue for nano-printing |
| WO2017101465A1 (en) * | 2015-12-15 | 2017-06-22 | 南方科技大学 | Nanoimprinted photoresist and preparation method therefor |
| CN116478650A (en) * | 2023-04-27 | 2023-07-25 | 江苏斯迪克新材料科技股份有限公司 | Normal-temperature high-modulus ultraviolet impression compound and preparation method thereof |
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