CN111123647A - Dry film photoresist and application thereof - Google Patents
Dry film photoresist and application thereof Download PDFInfo
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- CN111123647A CN111123647A CN202010035171.3A CN202010035171A CN111123647A CN 111123647 A CN111123647 A CN 111123647A CN 202010035171 A CN202010035171 A CN 202010035171A CN 111123647 A CN111123647 A CN 111123647A
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- 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
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- 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
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
- H05K3/06—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding the conductive material being removed chemically or electrolytically, e.g. by photo-etch process
- H05K3/061—Etching masks
- H05K3/064—Photoresists
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- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials For Photolithography (AREA)
- Manufacturing Of Printed Circuit Boards (AREA)
Abstract
The invention discloses a dry film photoresist and application thereof. The dry film photoresist comprises the following components in parts by mass: 50-70 parts of alkali-soluble acrylic resin, 20-50 parts of photopolymerization monomer, 0.1-3 parts of photoinitiator and a proper amount of additive; wherein the photopolymerization monomer consists of long-chain diacrylate containing diphenyl sulfide and short-chain acrylate; the short-chain acrylic ester is acrylic ester with the main chain carbon number less than or equal to 16. The invention also discloses application of the dry film photoresist in preparing photosensitive dry films and printed circuit boards. The photosensitive dry film prepared by the dry film photoresist has the advantages of high photosensitive speed, high resolution, good hole masking performance and wide market prospect.
Description
Technical Field
The invention relates to the technical field of photosensitive materials, in particular to a dry film photoresist and application thereof.
Background
The dry film is a photosensitive material, consists of three parts of a polyester film, a photoresist film and a polyethylene protective film, is widely applied to pattern electroplating processes of circuit board printing and the like, and is used for manufacturing precise fine wires and the like. In the manufacture of a printed wiring board, a dry film resist is first bonded to a copper substrate, and the dry film resist is covered with a mask having a predetermined pattern, followed by pattern exposure. Then, using weak alkaline aqueous solution as developing solution to remove unexposed part, then implementing etching or electroplating treatment to form pattern, finally stripping off by remover to remove dry film solidified part so as to implement pattern transfer. Photoresist systems generally consist of four parts: photosensitive resin (photopolymer), photoinitiator, photopolymerization monomer and additive.
In recent years, as electronic devices have been made thinner and smaller, the line size of patterns such as printed circuit boards mounted thereon has been smaller, and the contact area between a substrate and a resin composition on which patterns have been formed has been becoming smaller. In order to manufacture such a narrow-pitch wiring pattern with higher yield, a higher demand is placed on the dry film resist.
JP 2001-117225A discloses a dry film photoresist with good hole-masking property, wherein a photopolymerizable monomer having more than 3 ethylenically unsaturated bonds per molecule is introduced into the photoresist, and these polyfunctional monomers are liable to cause shrinkage during curing, thereby affecting the hole-masking and plating properties. US7517636 reports a new dry film with good hole-masking ability and stripping properties, but unfortunately the presence of long alkoxy chain acrylate monomers limits the resolution enhancement. US5744282 mentions that when using a photopolymerizable monomer such as isocyanuric acid, urethane, etc., a certain flexibility is exhibited. The current commercial applications require further improvement in flexibility and require maintaining the peeling ability of the cured film; CN99126102A reports a photosensitive dry film with strong flexibility, but the resolution is low, and the current industry requirements are difficult to meet. CN104834182A reports a photosensitive dry film prepared by using alkali soluble resin with specific molecular weight and molecular weight distribution, which has good high resolution and excellent hole masking property, however, the alkali soluble resin in this scheme is prepared by reversible addition-fragmentation chain transfer polymerization, and is not easy to realize mass production.
Disclosure of Invention
In order to overcome the problems of the prior art, an object of the present invention is to provide a dry film photoresist, and an object of the present invention is to provide an application of the dry film photoresist.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a dry film photoresist comprises the following components in parts by mass: 50-70 parts of alkali-soluble acrylic resin, 20-50 parts of photopolymerization monomer, 0.1-3 parts of photoinitiator and a proper amount of additive; wherein the photopolymerization monomer consists of long-chain diacrylate containing diphenyl sulfide and short-chain acrylate; the short-chain acrylic ester is acrylic ester with the main chain carbon number less than or equal to 16.
Preferably, in the dry film photoresist, the alkali-soluble acrylic resin has a structural formula shown in formula (1):
in the formula (1), a, b and c independently represent the mass ratio of three units in the alkali-soluble resin; wherein a is 40-60; b is 18-23; c is 20-30; r1、R2、R3Each independently represents a H atom or a methyl group; r4Is an alkyl chain having 1 to 12 carbon atoms.
Preferably, in the dry film photoresist, the number average molecular weight of the alkali soluble acrylic resin is 80000-140000; more preferably, the number average molecular weight of the alkali-soluble acrylic resin is 80000 to 100000.
In such a dry film photoresist, the alkali-soluble acrylic resin may be prepared by a solution polymerization method, or a commercial resin may be directly used.
Preferably, in the photopolymerizable monomer of the dry film photoresist, the mass ratio of the long-chain diacrylate containing diphenyl sulfide to the short-chain acrylate is 1: (0.5-2).
Preferably, in the photopolymerizable monomer, the structural formula of the diphenyl sulfide-containing long-chain diacrylate is shown in formula (2):
in the formula (2), n is a positive integer.
Preferably, in formula (2), n is 1 to 3.
In the photopolymerization monomer, short-chain acrylate is acrylate with the main chain carbon atom number less than or equal to 16, and can be subjected to polymerization or crosslinking reaction after absorbing light energy. Such short chain acrylates may be di-monofunctional or multifunctional. Preferably, the short-chain acrylate is selected from at least one of bisphenol a di (meth) acrylate, ethoxylated (propoxylated) bisphenol a di (meth) acrylate, polyethylene (propylene) glycol diacrylate, ethoxylated (propoxylated) neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate, trimethylolpropane triacrylate, ethoxylated (propoxylated) trimethylolpropane triacrylate, propoxylated glycerol triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate; further preferably, the short-chain acrylate is at least one selected from the group consisting of 1, 6-hexanediol diacrylate, trimethylolpropane triacrylate, propoxylated glycerol triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, pentaerythritol triacrylate and pentaerythritol tetraacrylate. In some preferred embodiments of the present invention, the short chain acrylate is trimethylolpropane triacrylate.
Preferably, in the dry film photoresist, the photoinitiator is at least one selected from benzoin compounds, benzophenone compounds, thioxanthone compounds, anthraquinone compounds, acylphosphine oxide compounds, thioxanthone compounds, hexaarylbisimidazole compounds and 9-phenylacridine compounds; further preferably, the photoinitiator is selected from the group consisting of benzoin bismethyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin phenyl ether, thioxanthone, 2-chlorothioxanthone, 4-chlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, benzophenone, 4' -bis (dimethylamino) benzophenone, 4' -bis (diethylamino) benzophenone, isopropylthioxanthone, 2-chlorothioxanthone, 2, 4-diethylthioxanthone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, ethyl N, N-dimethylbenzoate, dimethylaminoethyl benzoate, N-dimethylethanolamine, 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 2 ' -bis (2-chlorophenyl) -4, 4', 5,5 ' -tetraphenyl-1, 2 ' -diimidazole, 2 ' -bis (2-bromo-5-methoxybenzene) -4, 4', 5,5 ' -tetraphenyldiimidazole, 2 ' -bis (2, 4-dichlorophenyl) -4, 4', 5,5 ' -tetraphenyldiimidazole, 2 ', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4 ', 5 ' -diphenyl-1, 1 ' -diimidazole. In some preferred embodiments of the present invention, the photoinitiator is 2,2 ', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4', 5 '-diphenyl-1, 1' -diimidazole and 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide.
Preferably, the additive is used in an amount of 0.1 to 0.6 parts by mass in the dry film photoresist.
Preferably, in the dry film photoresist, the additive is selected from one or more of a coloring agent, a developing agent, a leveling agent, an antioxidant, a plasticizer, a tackifier, a stabilizer, a corrosion inhibitor and a polymerization inhibitor. The additives belong to common raw materials in the field and can be selected and added according to actual needs. For example, the coloring agent may be selected from basic green 1, basic green 2, basic green 3, basic green 4, basic green 5, tribromomethylphenyl sulfone, phthalocyanine blue or methyl orange. The corrosion inhibitor can be selected from 4-hydroxybenzotriazole, 5-carboxyl benzotriazole, 1-thioglycerol, 2-mercaptopropionic acid or catechol. The polymerization inhibitor can be selected from hydroquinone or p-hydroxyanisole.
The invention also provides application of the dry film photoresist.
The application of the dry film photoresist in preparing a photosensitive dry film.
Further, a dry film photoresist may be used to prepare a resist layer of a photosensitive dry film.
A method for preparing a photosensitive dry film resist layer comprises the following steps: according to the composition of the dry film photoresist, alkali soluble acrylic resin, a photopolymerization monomer, a photoinitiator and an additive are mixed, then the mixture is mixed with a solvent to prepare a resist solution, and the resist solution is coated on the surface of a base film and cured to form a resist layer.
In the preparation method of the photosensitive dry film resist layer, the selected solvent is an organic solvent which can disperse or dissolve the components of the dry film photoresist and does not react with the components. Preferably, the solvent is at least one selected from the group consisting of alcohol solvents, ketone solvents, ether solvents, benzene solvents, and amide solvents; further preferably, the solvent is at least one selected from the group consisting of methanol, ethanol, isopropanol, acetone, methyl ethyl ketone, ethylene glycol methyl ether, toluene, and N, N-dimethylformamide.
Preferably, in the method for preparing the photosensitive dry film resist, the solid content of the resist solution is 10 wt% to 92 wt%.
Preferably, in the method for preparing the photosensitive dry film resist, the base film is a polyester film; further preferably, the base film is a polyethylene terephthalate (PET) film.
Preferably, in the preparation method of the photosensitive dry film resist layer, the curing method is drying, specifically drying and molding at 60-80 ℃.
And (3) attaching a film to the surface of the prepared anti-corrosion layer to obtain the photosensitive dry film.
Preferably, the preparation method of the photosensitive dry film is to adhere a Polyethylene (PE) film to the surface of the resist layer to form the photosensitive dry film. The photosensitive dry film has a three-layer structure of a base film layer, a resist layer and a PE layer which are sequentially stacked.
The invention also provides application of the dry film photoresist in preparing a printed circuit board.
The invention has the beneficial effects that:
the photosensitive dry film prepared by the dry film photoresist has the advantages of high photosensitive speed, high resolution, good hole masking performance and wide market prospect.
Specifically, the present invention has the following advantages:
1. the invention selects alkali-soluble acrylic resin, combines the long-chain diacrylate containing diphenyl sulfide with the short-chain acrylate, and improves the resolution and the hole masking performance of the photoresist.
2. The long-chain diacrylate containing the diphenyl sulfide has a self-initiation effect, and the photosensitive speed of the photoresist can be improved by matching with a proper photoinitiator.
3. The dry film photoresist can reduce the occurrence of hole breakage phenomenon in the production of high-precision circuit boards, effectively improve the yield and efficiency of circuit board manufacture and reduce the manufacturing cost.
Detailed Description
The present invention will be described in further detail with reference to specific examples. The starting materials, reagents or apparatus used in the examples and comparative examples were obtained from conventional commercial sources or can be obtained by a method of the prior art, unless otherwise specified. Unless otherwise indicated, the testing or testing methods are conventional in the art.
The main reagent names and abbreviations used in the examples and comparative examples are as follows:
TBHDA: 4,4' -dimercapto phenyl sulfide hexyl ester diacrylate;
TMPTA: trimethylolpropane triacrylate;
TCDDB: 2,2 ', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4', 5 '-diphenyl-1, 1' -diimidazole;
omnirad TPO: 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide.
The structural formula of the reagent is shown in Table 1.
TABLE 1 names, abbreviations and structural formulae of reagents
Table 2 shows formulation composition tables of dry film photoresists of examples and comparative examples, and the usage units shown in table 2 are parts by mass.
TABLE 2 formulation tables for examples and comparative examples
| Raw materials | Example 1 | Example 2 | Example 3 | Comparative example 1 | Comparative example 2 |
| Acrylic resin | 66.5 | 66.5 | 66.5 | 66.5 | 66.5 |
| TBHDA | 5 | 10 | 15 | - | 5 |
| TMPTA | 15 | 10 | 5 | 20 | 15 |
| TCDDB | 2 | 2 | 2 | 2 | 3 |
| Omnirad TPO | 1 | 1 | 1 | 1 | - |
| Alkaline Green 1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
| Tribromomethyl phenyl sulfone | 0.29 | 0.29 | 0.29 | 0.29 | 0.29 |
| 5-carboxybenzotriazoles | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
| Hydroquinone | 0.01 | 0.01 | 0.01 | 0.01 | 0.01 |
| Acetone (II) | 10 | 10 | 10 | 10 | 10 |
The acrylic resin is alkali soluble acrylic resin, the structural formula is shown in formula (3), and the specific number average molecular weight is 100000.
The resist solutions of examples 1 to 3 and comparative examples 1 to 2 were obtained by mixing the components of the dry film photoresist except the solvent acetone in parts by mass, then mixing with acetone, stirring uniformly at room temperature, and removing impurities with a 200-mesh filter.
The resist solutions of examples 1 to 3 and comparative examples 1 to 2 were uniformly coated on a 15 μm PET film (double-sided heat seal type) using a bar coater, and after drying at 70 ℃, a resist layer was formed. Then, an 18 μm-thick PE film was heat-laminated on the resist surface using a rubber roll to obtain a dry film having a thickness of 40 μm of the photosensitive resin composition layer.
The prepared photosensitive dry film was tested:
a 40 μm thick photosensitive resin layer was used to evaluate the resolution and side profile after dry film development.
Film pasting: the film was applied using a 27-22808-A3 film press from Mega Electronics Ltd. of UK at a speed of 1 m/min and a temperature of 90 ℃.
Exposure: exposing with M552 exposure machine, measuring exposure energy with 21 lattice exposure ruler, and measuring exposure energy with 7-10 lattices and 30-60mJ/cm2。
And (3) developing: development was carried out using HM-BL258 developing machine of Guangzhou constant Electron Ltd. Gradually increasing the line width/line distance of the film selected by developing from 10 mu m to 100 mu m; the developing solution is 1% sodium carbonate aqueous solution, the developing temperature is 30 ℃, the developing pressure is 1.8bar, and the developing speed is 1.5 m/min.
The samples were observed by SEM at 500 x magnification.
Evaluation of photosensitive speed: the dry film exposure speed was measured by using a UVE-HSP5K manual parallel light exposure machine of Histo opto-electronic technology Co., Ltd, Dongguan.
And (3) evaluating the resolution: after exposure and development were performed using a photomask of a wiring pattern with an equal Line pitch and an equal Line width of Line/Space of 10/10 to 100/100 μm, observation was performed using an optical microscope, and the minimum Line width at which the side profile was good and the full development was clear was evaluated.
Evaluation of adhesion: after exposure and development were performed using a photomask having a Line/Space of n/400(n is 10 to 50) μm wiring pattern, observation was performed using an optical microscope, and the minimum Line width with good side profile and complete and clear Line was evaluated.
Evaluation of hole-masking ability: the dry film resist was peeled off the protective film and laminated on a multi-well plate, wherein 100 triple wells (16X 6mm) having a diameter of 6mm and 100 quadruple wells (21X 6mm) having a diameter of 6mm were formed. And (4) exposing by using exposure energy when the number of the photosensitive grids is 8, developing by using 4 times of the shortest developing time, and counting the hole breaking rate.
The test evaluation results are shown in table 3.
TABLE 3 test evaluation results
From the results in table 3, it can be seen that: compared with the samples of comparative examples 1-2, the samples of examples 1-3 have the advantages of smaller exposure energy, higher photospeed, higher resolution, lower porosity of 6mm triple holes (16 × 6mm) and 6mm quadruple holes (21 × 6mm), and better hole masking performance. It can be seen that the dry film photoresist of the present invention has higher quality.
In practical application, the dry film photoresist can reduce the occurrence of hole breaking phenomenon in the production of high-precision circuit boards, effectively improve the yield and efficiency of circuit board manufacturing and reduce the manufacturing cost. The dry film photoresist can be widely applied to the fields of manufacturing of printed circuit boards, lead frames and the like, manufacturing of semiconductor packages and the like.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A dry film photoresist, characterized by: the paint comprises the following components in parts by mass: 50-70 parts of alkali-soluble acrylic resin, 20-50 parts of photopolymerization monomer, 0.1-3 parts of photoinitiator and a proper amount of additive;
the photopolymerization monomer consists of long-chain diacrylate containing diphenyl sulfide and short-chain acrylate; the short-chain acrylic ester is acrylic ester with the main chain carbon atom number less than or equal to 16.
2. The dry film photoresist according to claim 1, wherein: the structural formula of the alkali-soluble acrylic resin is shown as the formula (1):
in the formula (1), a is 40-60; b is 18-23; c is 20-30; r1、R2、R3Each independently represents a H atom or a methyl group; r4Is an alkyl chain having 1 to 12 carbon atoms.
3. The dry film photoresist according to claim 1, wherein: in the photopolymerization monomer, the mass ratio of the long-chain diacrylate containing the diphenyl sulfide to the short-chain acrylate is 1: (0.5-2).
4. The dry film photoresist according to claim 3, wherein: the structural formula of the long-chain diacrylate containing the diphenyl sulfide is shown as the formula (2):
(2) (ii) a In the formula (2), n is a positive integer.
5. The dry film photoresist according to claim 3, wherein: the short-chain acrylate is selected from at least one of bisphenol A di (methyl) acrylate, ethoxylated (propylene oxide) bisphenol A di (methyl) acrylate, polyethylene (propylene) glycol diacrylate, ethoxylated (propylene oxide) neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate, trimethylolpropane triacrylate, ethoxylated (propylene oxide) trimethylolpropane triacrylate, propoxylated glycerol triacrylate, tris (2-hydroxyethyl) isocyanurate triacrylate, pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate and dipentaerythritol hexaacrylate.
6. The dry film photoresist according to claim 1, wherein: the photoinitiator is at least one selected from benzoin compounds, benzophenone compounds, thioxanthone compounds, anthraquinone compounds, acylphosphine oxide compounds, thioxanthone compounds, hexaarylbisimidazole compounds and 9-phenylacridine compounds.
7. The dry film photoresist according to claim 1, wherein: the additive is used in an amount of 0.1 to 0.6 parts by mass.
8. The dry film photoresist according to claim 7, wherein: the additive is selected from one or more of a coloring agent, a developing agent, a leveling agent, an antioxidant, a plasticizer, a tackifier, a stabilizer, a corrosion inhibitor and a polymerization inhibitor.
9. Use of the dry film photoresist according to any one of claims 1 to 8 for preparing a photosensitive dry film.
10. Use of the dry film photoresist of any one of claims 1 to 8 for the preparation of printed circuit boards.
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| CN113176706A (en) * | 2021-04-27 | 2021-07-27 | 浙江福斯特新材料研究院有限公司 | Dry film resist composition |
| CN113176706B (en) * | 2021-04-27 | 2024-05-28 | 杭州福斯特电子材料有限公司 | Dry film resist composition |
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