CN111123647B - Dry film photoresist and application thereof - Google Patents
Dry film photoresist and application thereof Download PDFInfo
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- CN111123647B CN111123647B CN202010035171.3A CN202010035171A CN111123647B CN 111123647 B CN111123647 B CN 111123647B CN 202010035171 A CN202010035171 A CN 202010035171A CN 111123647 B CN111123647 B CN 111123647B
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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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- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Spectroscopy & Molecular Physics (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 phenyl 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 and high resolution, and meanwhile, has good hole masking performance and very broad 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, and is composed of a polyester film, a photoresist film and a polyethylene protective film, and is widely applied to pattern electroplating processes such as circuit board printing and the like for manufacturing precise fine wires and the like. In manufacturing a printed circuit board, first, a dry film resist is laminated on a copper substrate, and the dry film resist is covered with a mask having a predetermined pattern, and pattern exposure is performed. Then, the unexposed parts are removed by using a weak alkaline aqueous solution as a developing solution, etching or electroplating is performed to form a pattern, and finally, the dry film cured part is peeled off and removed by using a remover, thereby realizing pattern transfer. Photoresist systems generally consist of four parts: a photosensitive resin (photopolymer), a photoinitiator, a photopolymerizable monomer and additives.
In recent years, as electronic devices have been made thinner and smaller, the line size of a pattern such as a printed circuit board mounted thereon has been made smaller, and the contact area between a substrate and a resin composition on which the pattern has been formed has been made smaller. In order to manufacture such a narrow-pitch wiring pattern with higher yield, this places higher demands on the dry film resist.
JP-A2001-117225 discloses a dry film photoresist having good hole-masking properties, in which a photopolymerizable monomer having 3 or more ethylenic unsaturated bonds per molecule is incorporated into the resist, and these polyfunctional monomers are extremely liable to cause shrinkage upon curing, thereby affecting hole-masking and plating properties. US7517636 reports a novel dry film with good hole masking and stripping properties, however unfortunately the presence of long alkoxy chain acrylate monomers limits the resolution improvement. US5744282 mentions that certain flexibility is exhibited when using photopolymerizable monomers such as isocyanuric acid, carbamates, etc. Current commercial applications require further improvements in flexibility and the need to maintain the release ability of the cured film; CN99126102a reports a photosensitive dry film with strong flexibility, but with low resolution, it is difficult to meet the current industry demands. CN104834182a reports a photosensitive dry film prepared using an alkali-soluble resin of a specific molecular weight and molecular weight distribution, which has a good high resolution and excellent hole-masking properties, 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, one of the purposes of the present invention is to provide a dry film photoresist, and the other purpose of the present invention is to provide an application of the dry film photoresist.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
a dry film photoresist comprising 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 phenyl 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 respectively and independently represent the mass ratio of three units in the alkali-soluble resin; wherein a=40 to 60; b=18 to 23; c=20 to 30; r is R 1 、R 2 、R 3 Each independently represents an H atom or a methyl group; r is R 4 Is an alkyl chain having 1 to 12 carbon atoms.
Preferably, in the dry film photoresist, the alkali-soluble acrylic resin has a number average molecular weight of 80000 to 140000; more preferably, the alkali-soluble acrylic resin has a number average molecular weight of 80000 to 100000.
In the dry film photoresist, the alkali-soluble acrylic resin can be prepared by a solution polymerization method, and can also be directly used as a commercial resin.
Preferably, in the photopolymerizable monomer of the dry film photoresist, the mass ratio of the long-chain diacrylate containing the phenyl sulfide to the short-chain acrylate is 1: (0.5-2).
Preferably, in the photopolymerization monomer, the structural formula of the long-chain diacrylate containing the phenyl sulfide is shown as the formula (2):
in the formula (2), n is a positive integer.
Preferably, in formula (2), n=1 to 3.
In the photopolymerization monomer, the short-chain acrylic ester is acrylic ester with the main chain carbon number less than or equal to 16, and can be polymerized or crosslinked after absorbing light energy. Such short-chain acrylates may be di-mono-functional compounds or multi-functional compounds. 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) isocyanuric acid 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, glycerol triacrylate, tris (2-hydroxyethyl) isocyanuric acid triacrylate, pentaerythritol tetraacrylate. In some preferred embodiments of the present invention, the short chain acrylate is selected from trimethylolpropane triacrylate.
Preferably, in the dry film photoresist, the photoinitiator is at least one selected from benzoin compounds, benzophenone compounds, thioxanthone compounds, anthraquinone compounds, acyl phosphine oxide compounds, thioxanthone compounds, hexaarylbisimidazole compounds and 9-phenylacridine compounds; further preferred photoinitiators are selected from benzoin dimethyl ether, benzoin diethyl 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-t-butylanthraquinone, N, ethyl N-dimethylbenzoate, dimethylaminoethyl benzoate, N-dimethylethanolamine, 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 2 '-bis (2-chlorophenyl) -4,4',5 '-tetraphenyl-1, 2' -diimidazole, 2 '-bis (2-bromo-5-methoxybenzene) -4,4', at least one of 5,5 '-tetraphenyldiimidazole, 2' -bis (2, 4-dichlorophenyl) -4,4', 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 selected from the group consisting of 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 dry film photoresist is used in an amount of 0.1 to 0.6 parts by mass.
Preferably, in the dry film photoresist, the additive is one or more selected from a coloring agent, a developer, a leveling agent, an antioxidant, a plasticizer, a tackifier, a stabilizer, a corrosion inhibitor and a polymerization inhibitor. These additives are all common raw materials in the field, and can be 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 may be selected from 4-hydroxybenzotriazole, 5-carboxybenzotriazole, 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 dry film photoresist is applied to the preparation of a photosensitive dry film.
Further, dry film photoresists may be used to prepare resist layers that photosensitive dry films.
A preparation method of 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 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, 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 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, butanone, ethylene glycol methyl ether, toluene, and N, N-dimethylformamide.
Preferably, in the preparation method of the photosensitive dry film resist layer, the solid content of the resist solution is 10-92 wt%.
Preferably, in the preparation method of the photosensitive dry film resist layer, 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, and particularly, drying and forming are carried out at 60-80 ℃.
And (3) attaching a film on the surface of the prepared anti-corrosion layer to prepare a photosensitive dry film.
Preferably, a photosensitive dry film is prepared by laminating a Polyethylene (PE) film on the surface of the resist layer. The photosensitive dry film has a three-layer structure, namely a base film layer, a resist layer and a PE layer which are sequentially overlapped.
The invention also provides application of the dry film photoresist in preparation of a printed circuit board.
The beneficial effects of the invention are as follows:
the photosensitive dry film prepared by the dry film photoresist has the advantages of high photosensitive speed and high resolution, and meanwhile, has good hole masking performance and very broad market prospect.
In particular, the invention has the following advantages:
1. the invention selects the acrylic resin with alkali solubility, and uses the long-chain diacrylate containing phenyl sulfide and the short-chain acrylate in a matching way, thereby improving the resolution ratio and the hole masking performance of the photoresist.
2. The long-chain diacrylate containing the phenyl 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 breaking 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 either commercially available from conventional sources or may be obtained by prior art methods unless specifically indicated. Unless otherwise indicated, assays or testing methods are routine in the art.
The main reagent names and abbreviations used in the examples and comparative examples are as follows:
TBHDA:4,4' -dimercaptophenyl sulfide hexyl 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-diphenyl phosphine oxide.
The structural formula of the reagent is shown in table 1.
Table 1 names, abbreviations and structural formulas of reagents
Table 2 shows the formulation composition of dry film photoresists of examples and comparative examples, and the dosage units shown in Table 2 are parts by mass.
Table 2 formulation tables of 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 green1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
| Tribromomethylphenyl sulfone | 0.29 | 0.29 | 0.29 | 0.29 | 0.29 |
| 5-carboxybenzotriazoles | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
| Hydroquinone (HQ) | 0.01 | 0.01 | 0.01 | 0.01 | 0.01 |
| Acetone (acetone) | 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.
According to the mass parts of the components in Table 2, the dry film photoresist components other than the solvent acetone were mixed, then mixed with acetone, stirred uniformly at room temperature, and filtered through a 200-mesh filter to remove impurities, thereby obtaining resist solutions of examples 1 to 3 and comparative examples 1 to 2.
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) using a bar coater, and dried at 70℃to form a resist layer. Then, a PE film having a thickness of 18 μm was heat-bonded to the surface of the resist layer by using a rubber roll, thereby obtaining a dry film having a photosensitive resin composition layer thickness of 40. Mu.m.
The prepared photosensitive dry film is tested:
a 40 μm thick photosensitive resin layer was used to evaluate resolution and side morphology after dry film development.
Sticking film: the film was attached using a 27-22808-A3 laminator of Mega Electronics Ltd. In UK at an attachment speed of 1 m/min and an attachment temperature of 90 ℃.
Exposure: exposing with a Saint science and technology M552, measuring exposure energy with a stop 21-grid exposure ruler, wherein the number of exposure grids is 7-10, and the exposure energy is 30-60mJ/cm 2 。
Developing: development was performed using an HM-BL258 developing machine from Hengming electronics, inc. of Guangzhou. Developing the selected film line width/line distance gradually increased from 10 μm to 100 μm; the developing solution was 1% sodium carbonate aqueous solution, the developing temperature was 30 ℃, the developing pressure was 1.8bar, and the developing speed was 1.5 m/min.
The sample was observed by SEM at 500 x magnification.
And (3) evaluating the photosensitive speed: the dry film exposure speed was measured using a UVE-HSP5K manual parallel light exposure machine from Heisha phototechnology Co., dongguan.
Resolution evaluation: after performing exposure development using a photomask of a wiring pattern having a Line/space=10/10 to 100/100 μm and an equal Line width, the Line was observed with an optical microscope, and the minimum Line width at which the side profile was good and the Line width was completely developed and clear was evaluated.
Adhesion evaluation: after performing exposure development using a photomask of a wiring pattern of Line/space=n/400 (n=10-50) μm, observation was performed with an optical microscope, and the minimum Line width with good side morphology and complete and clear Line was evaluated.
Hole masking ability evaluation: the dry film resist was peeled off and laminated on a multi-well plate, wherein three connecting holes (16X 6 mm) of 6mm in diameter were 100 and four connecting holes (21X 6 mm) of 6mm in diameter were 100. Exposing with exposure energy when the number of photosensitive grids is 8, developing with the length of 4 times of the shortest development 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: the samples of examples 1 to 3 used smaller exposure energy, faster photospeed, higher resolution, and lower hole breaking ratios of 6mm triple holes (16X 6 mm) and 6mm quadruple holes (21X 6 mm) and better hole masking performance than the samples of comparative examples 1 to 2. 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 printed circuit boards, lead frames and the like, manufacturing semiconductor packages and the like.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (7)
1. A dry film photoresist, characterized by: 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 structural formula of the alkali-soluble acrylic resin is shown as a formula (1):
in the formula (1), a=40 to 60; b=18 to 23; c=20 to 30; r is R 1 、R 2 、R 3 Each independently represents an H atom or a methyl group; r is R 4 Is an alkyl chain having 1 to 12 carbon atoms;
the photopolymerization monomer consists of long-chain diacrylate containing phenyl 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 structural formula of the long-chain diacrylate containing the phenyl sulfide is shown as the formula (2):
(2) The method comprises the steps of carrying out a first treatment on the surface of the In the formula (2), n=1 to 3;
the photoinitiator is an acyl phosphine oxide compound and a hexaaryl bisimidazole compound.
2. A dry film photoresist according to claim 1, wherein: in the photopolymerization monomer, the mass ratio of the long-chain diacrylate containing the phenyl sulfide to the short-chain acrylate is 1: (0.5-2).
3. A dry film photoresist according to claim 2, wherein: the short-chain acrylic ester is at least one selected from bisphenol A dimethacrylate, ethoxylated bisphenol A dimethacrylate, propoxylated bisphenol A dimethacrylate, polyethylene glycol diacrylate, polypropylene glycol diacrylate, ethoxylated neopentyl glycol diacrylate, propoxylated neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate, trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated glycerol triacrylate, tri (2-hydroxyethyl) isocyanuric acid triacrylate, pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate and dipentaerythritol hexaacrylate.
4. A dry film photoresist according to claim 1, wherein: the dosage of the additive is 0.1 to 0.6 part by mass.
5. A dry film photoresist according to claim 4, wherein: the additive is one or more selected from a coloring agent, a developer, a leveling agent, an antioxidant, a plasticizer, a tackifier, a stabilizer, a corrosion inhibitor and a polymerization inhibitor.
6. Use of a dry film photoresist according to any one of claims 1 to 5 for the preparation of a photosensitive dry film.
7. Use of a dry film photoresist according to any one of claims 1 to 5 for the preparation of printed circuit boards.
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