CN112650024A - High-film-thickness negative photoresist applied to chip packaging process - Google Patents

High-film-thickness negative photoresist applied to chip packaging process Download PDF

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CN112650024A
CN112650024A CN202011491006.5A CN202011491006A CN112650024A CN 112650024 A CN112650024 A CN 112650024A CN 202011491006 A CN202011491006 A CN 202011491006A CN 112650024 A CN112650024 A CN 112650024A
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negative photoresist
chip packaging
packaging process
photoresist applied
photoinitiator
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CN112650024B (en
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卞玉桂
向文胜
张兵
赵建龙
朱坤
陆兰
顾群艳
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Jiangsu Aisen Semiconductor Material Co ltd
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Jiangsu Aisen Semiconductor Material Co ltd
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/038Macromolecular compounds which are rendered insoluble or differentially wettable
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H01L21/0271Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers

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  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Materials For Photolithography (AREA)

Abstract

The invention discloses a high-film-thickness negative photoresist applied to a chip packaging process, which comprises 20-60% of acrylic resin, 8-40% of an initiator, 10-30% of a cross-linking agent, 100-1000 ppm of a leveling agent and 30-70% of a solvent; wherein the acrylic resin comprises a molecular weight of 5000-50000 and a distribution of 1.2-3.0; the cross-linking agent has a molecular weight of 500-2500, and the leveling agent has a molecular weight of 3000-6000. When the invention is used for coating a higher film thickness, the patterning effect can be ensured, the process requirement is met, and the coating uniformity is improved.

Description

High-film-thickness negative photoresist applied to chip packaging process
[ technical field ] A method for producing a semiconductor device
The invention belongs to the technical field of photoresist for chip packaging, and particularly relates to a high-film-thickness negative photoresist applied to a chip packaging process.
[ background of the invention ]
Negative photoresist is a patterned transfer tool, a composition of resin, photosensitive compound, additives, solvent, which, upon exposure to ultraviolet light, forms crosslinks in the exposed portions, which are insoluble in the developer, while the unexposed portions dissolve, thus forming the desired image.
The high-film-thickness negative photoresist is characterized by unique design, higher film thickness requirement, coating uniformity within 10 percent, required profile angle controlled within 88-90 degrees, and the like, and has the characteristics of copper electroplating resistance.
Satisfying the above characteristic elements, it is necessary to make sufficient studies on photoresist raw materials such as resin, initiator, leveling agent, crosslinking agent, etc., and combine them to obtain optimized conditions. The difficulty of the research of the negative photoresist lies in how to ensure the patterning effect while keeping higher film thickness, and the photoresist needs to resist the corrosion of copper, nickel and tin-silver electroplating silver, the surface of the photoresist does not crack, and the angle is steep after electroplating. When the coating thickness of the negative photoresist in the prior art reaches more than 105 micrometers, the problems of poor coating uniformity, incapability of enduring an electroplating process, surface cracking of an electroplated adhesive film and the like easily occur, so that a novel high-film-thickness negative photoresist applied to a chip packaging process needs to be provided to solve the problems.
[ summary of the invention ]
The invention mainly aims to provide a high-film-thickness negative photoresist applied to a chip packaging process, which can ensure a patterning effect when a higher film thickness is coated, meet the process requirement and improve the coating uniformity.
The invention realizes the purpose through the following technical scheme: a high-film-thickness negative photoresist applied to a chip packaging process comprises 20-60% of acrylic resin, 8-40% of an initiator, 10-30% of a cross-linking agent, 100-1000 ppm of a leveling agent and 30-70% of a solvent; wherein the acrylic resin comprises a molecular weight of 5000-50000 and a distribution of 1.2-3.0; the cross-linking agent has a molecular weight of 500-2500, and the leveling agent has a molecular weight of 3000-6000.
Further, the acrylic resin has a structural formula:
Figure BDA0002840688350000021
wherein R is1、R2、R3、R4Is H, CH3、CH2CH3One or more of COOH, benzoic acid, styrene, butadiene and isoprene.
The mass percentage of the acrylic resin is preferably 30-50%, and the coating film thickness of the product can be influenced by too high or too low content of the acrylic resin.
Further, the photoinitiator comprises a photoinitiator A and a photoinitiator B, wherein the photoinitiator A is 4-20% by mass, and the photoinitiator B is 4-20% by mass.
Further, the structural formula of the photoinitiator A is as follows:
Figure BDA0002840688350000022
wherein R is1、R2、R3、R4Is H, CH3、OH、CH2CH3And COOH or a mixture of a plurality of COOH. The mass percentage of the material is preferably 5-15%, and the exposure performance of the product can be affected by too high or too low content.
Further, the structural formula of the photoinitiator B is as follows:
Figure BDA0002840688350000023
wherein R is1、R2、R3、R4、R5Is H, CH3、OH、CH2CH3And COOH or a mixture of a plurality of COOH. The mass percentage of the material is preferably 5-10%, and the exposure performance of the product can be affected by too high or too low content.
Further, the structural formula of the cross-linking agent is as follows:
Figure BDA0002840688350000031
wherein R is1、R2、R3Is H, CH3、OH、CH2CH3One or more, n is 1-6. The molecular weight of the cross-linking agent is 500-2500, and the cross-linking degree of the product can be influenced by excessively high or excessively low molecular weight. The mass percentage of the ink is between 10 and 30 percent, and the mass percentage can influence the imaging performance of the product.
Further, the leveling agent is a polydimethylsiloxane copolymer solution, the mass percentage of the polydimethylsiloxane copolymer solution is preferably 300-700 ppm, and the coating uniformity of the product is affected by too high or too low content of the polydimethylsiloxane copolymer solution.
Further, the solvent is one or a mixture of propylene glycol methyl ether acetate, 3-methoxy acrylate, diethylene glycol dimethyl ether and ethyl lactate, the mass percentage of the solvent is preferably 30-50%, and the coating performance of the product can be affected by too high or too low content.
When the coating is used, the acrylic resin, the crosslinking agent, the photoinitiator, the flatting agent and the solvent are combined in the proportioning range, and coated on a European 12inch silicon wafer in a spin coating mode, wherein the coating thickness is 110 mu m, and the coating uniformity is controlled within 5%; and after coating, baking, exposing and developing to obtain a required pattern, and then removing the photoresist through electroplating and photoresist removing processes to obtain the required electroplating pattern.
Compared with the prior art, the high-film-thickness negative photoresist applied to the chip packaging process has the beneficial effects that: by independently developing an acrylic resin structure containing the molecular weight of 5000-50000, the solid content of the photoresist is greatly increased, and the viscosity is reduced, so that the coating thickness of the photoresist is increased, and the coating uniformity is improved; the method ensures a good patterning effect while keeping a high film thickness, resists the corrosion of copper, nickel and tin-silver electroplating silver, has no cracking of a glue surface and steep electroplating rear angle, and meets the process requirement of high film thickness for chip packaging.
[ description of the drawings ]
FIG. 1 is a schematic view of a photoresist developed according to an embodiment of the present invention;
FIG. 2 is a schematic view of a photoresist stripped by electroplating according to an embodiment of the present invention.
[ detailed description ] embodiments
Example (b):
acrylic resin, a photoinitiator A, an initiator B, a crosslinking agent, a leveling agent and a solvent are added into a feeding kettle according to the formula in the table 1 and stirred for 24 hours, the mixture is dissolved and filtered, the thickness of the mixture is 110um coated on an 8inch copper sheet, and the uniformity, the exposure energy, the angle and the electroplating resistance are tested after the coating, and the results are shown in the table 2.
TABLE 1
Name of material Formulation 1 Formulation 2 Formulation 3 Formulation 4 Formulation 5
Acrylic resin 35 35 35 35 35
Initiator A 10 8 5 6 9
Initiator B 10 9 5 9 6
Crosslinking agent 10 13 20 15 15
Leveling agent 500ppm 600ppm 600ppm 500ppm 500ppm
Solvent(s) 35 35 35 35 35
TABLE 2
Film thickness um Uniformity of the composition Exposure energy mj/cm2 Angle degree after development Characteristics of plating
Formulation 1 110 4.06 1200~1650 89 OK
Formulation 2 108 3.53 1100~1500 88 OK
Formulation 3 106 3.52 900~1300 85 OK
Formulation 4 107 3.42 1100~1450 87 OK
Formulation 5 108 3.39 1100~1450 88 OK
Target 105~112 ≤5 1000~1800 ≥87
The photoresist prepared by the scheme is coated on a European 12inch silicon chip in a spin coating mode, the coating thickness is 110um, and the coating uniformity is controlled within 5%; and baking, exposing and developing after coating to obtain a required pattern, wherein the appearance schematic diagram after developing is shown in figure 1, and removing the photoresist through electroplating and photoresist removing processes to obtain the required electroplating pattern shown in figure 2. From the viewpoint of different photoresist formulations, the leveling agent affects the coating uniformity of the photoresist, the ratio of the photosensitizer to the cross-linking agent affects the exposure energy and the post-development angle, and the latitude is sufficient for a range of formulations. The photoresist prepared by the scheme can meet the coating requirement in the manufacture procedure of the PCB with high film thickness.
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 (8)

1. A high-film-thickness negative photoresist applied to a chip packaging process is characterized in that: it comprises 20 to 60 percent of acrylic resin, 8 to 40 percent of initiator, 10 to 30 percent of cross-linking agent, 100 to 1000ppm of flatting agent and 30 to 70 percent of solvent; wherein the acrylic resin comprises a molecular weight of 5000-50000 and a distribution of 1.2-3.0; the cross-linking agent has a molecular weight of 500-2500, and the leveling agent has a molecular weight of 3000-6000.
2. The high film thickness negative photoresist applied to a chip packaging process as claimed in claim 1, wherein: the structural formula of the acrylic resin is as follows:
Figure FDA0002840688340000011
wherein R is1、R2、R3、R4Is H, CH3、CH2CH3One or more of COOH, benzoic acid, styrene, butadiene and isoprene.
3. The high film thickness negative photoresist applied to a chip packaging process as claimed in claim 1, wherein: the photoinitiator comprises a photoinitiator A and a photoinitiator B, wherein the photoinitiator A is 4-20% by mass, and the photoinitiator B is 4-20% by mass.
4. The high film thickness negative photoresist applied to a chip packaging process as claimed in claim 3, wherein: the structural formula of the photoinitiator A is as follows:
Figure FDA0002840688340000012
wherein R is1、R2、R3、R4Is H, CH3、OH、CH2CH3And COOH or a mixture of a plurality of COOH.
5. The high film thickness negative photoresist applied to a chip packaging process as claimed in claim 3, wherein: the structural formula of the photoinitiator B is as follows:
Figure FDA0002840688340000021
wherein R is1、R2、R3、R4、R5Is H, CH3、OH、CH2CH3And COOH or a mixture of a plurality of COOH.
6. The high film thickness negative photoresist applied to a chip packaging process as claimed in claim 1, wherein: the structural formula of the cross-linking agent is as follows:
Figure FDA0002840688340000022
wherein R is1、R2、R3Is H, CH3、OH、CH2CH3One or more, n is 1-6.
7. The high film thickness negative photoresist applied to a chip packaging process as claimed in claim 1, wherein: the leveling agent is polydimethylsiloxane copolymer solution.
8. The high film thickness negative photoresist applied to a chip packaging process as claimed in claim 1, wherein: the solvent is one or a mixture of propylene glycol methyl ether acetate, 3-methoxy acrylate, diethylene glycol dimethyl ether and ethyl lactate.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114967340A (en) * 2021-02-22 2022-08-30 中国建材国际工程集团有限公司 Polypeptide type negative thick film photoresist and preparation and use method thereof
CN115138230A (en) * 2022-07-29 2022-10-04 江苏艾森半导体材料股份有限公司 Thick film negative photoresist and its preparing process
CN115710328A (en) * 2022-10-28 2023-02-24 江苏艾森半导体材料股份有限公司 High molecular weight acrylic resin

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CN1246655A (en) * 1998-08-18 2000-03-08 西巴特殊化学品控股有限公司 Sulfonic acid oxime kind for high light sensitivity high elch-resistant thick coating i-line photoetching rubber
CN1639641A (en) * 2002-02-28 2005-07-13 日立化成工业株式会社 Photosensitive resin composition, process for forming photosensitive elements or resist patterns with the same, and process for production of printed wiring boards
JP2005309451A (en) * 2001-05-21 2005-11-04 Tokyo Ohka Kogyo Co Ltd Negative photoresist composition for thick film, photoresist film and method for forming bump by using same
KR20070063457A (en) * 2005-12-14 2007-06-19 이 아이 듀폰 디 네모아 앤드 캄파니 Cationically polymerizable photoimageable thick film compositions, electrodes, and methods of forming thereof
CN102395924A (en) * 2009-04-30 2012-03-28 日立化成工业株式会社 Photosensitive resin composition, photosensitive element utilizing the composition, method for formation of resist pattern, and process for production of printed circuit board
CN103064254A (en) * 2011-10-20 2013-04-24 日立化成工业株式会社 Photosensitive resin compound, photosensitive component, formation method of resist pattern, and manufacturing method of printed circuit board
CN107219726A (en) * 2017-06-27 2017-09-29 浙江福斯特新材料研究院有限公司 A kind of resin combination and purposes

Patent Citations (7)

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Publication number Priority date Publication date Assignee Title
CN1246655A (en) * 1998-08-18 2000-03-08 西巴特殊化学品控股有限公司 Sulfonic acid oxime kind for high light sensitivity high elch-resistant thick coating i-line photoetching rubber
JP2005309451A (en) * 2001-05-21 2005-11-04 Tokyo Ohka Kogyo Co Ltd Negative photoresist composition for thick film, photoresist film and method for forming bump by using same
CN1639641A (en) * 2002-02-28 2005-07-13 日立化成工业株式会社 Photosensitive resin composition, process for forming photosensitive elements or resist patterns with the same, and process for production of printed wiring boards
KR20070063457A (en) * 2005-12-14 2007-06-19 이 아이 듀폰 디 네모아 앤드 캄파니 Cationically polymerizable photoimageable thick film compositions, electrodes, and methods of forming thereof
CN102395924A (en) * 2009-04-30 2012-03-28 日立化成工业株式会社 Photosensitive resin composition, photosensitive element utilizing the composition, method for formation of resist pattern, and process for production of printed circuit board
CN103064254A (en) * 2011-10-20 2013-04-24 日立化成工业株式会社 Photosensitive resin compound, photosensitive component, formation method of resist pattern, and manufacturing method of printed circuit board
CN107219726A (en) * 2017-06-27 2017-09-29 浙江福斯特新材料研究院有限公司 A kind of resin combination and purposes

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114967340A (en) * 2021-02-22 2022-08-30 中国建材国际工程集团有限公司 Polypeptide type negative thick film photoresist and preparation and use method thereof
CN115138230A (en) * 2022-07-29 2022-10-04 江苏艾森半导体材料股份有限公司 Thick film negative photoresist and its preparing process
CN115138230B (en) * 2022-07-29 2023-06-13 江苏艾森半导体材料股份有限公司 Thick film negative photoresist and photoresist preparation method
CN115710328A (en) * 2022-10-28 2023-02-24 江苏艾森半导体材料股份有限公司 High molecular weight acrylic resin

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