CN109828436B - High-adhesion etching-resistant photosensitive resin composition - Google Patents
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Abstract
The invention discloses a high-adhesion anti-etching photosensitive resin composition which mainly comprises 45-70 wt% of alkali-soluble copolymer resin with the weight-average molecular weight of 50,000-150,000, 15-45 wt% of olefinic photopolymerization unsaturated monomer, 1-10 wt% of photopolymerization initiator and 0.5-5 wt% of additive, wherein the alkali-soluble polymer resin is prepared by polymerizing cycloolefin anhydride containing a double six-membered ring rigid structure, (methyl) acrylic acid and acrylate compound free radicals. The photosensitive resin composition containing the alkali-soluble polymer resin has high adhesion, good resolution and etching resistance, effectively reduces the occurrence of a breaking phenomenon in an etching process, and greatly improves the yield and efficiency in the production process of PCBs.
Description
Technical Field
The invention relates to a resin composition, in particular to a high-adhesion and anti-corrosion photosensitive resin composition.
Background
Dry Film Resists (DFR), which are widely used as key materials for pattern transfer in printed circuit boards, lead frames, semiconductor encapsulating materials, are often prepared by laminating a photosensitive resin composition on a support and then covering the photosensitive resin composition with a protective layer as needed. The photosensitive resin composition is a DFR core and is generally composed of an alkali-soluble resin polymer having a carboxyl group, an ethylenic photopolymerizable monomer having at least one terminal ethylenically unsaturated group, a photopolymerization initiator and other additives by mixing.
When a printed wiring board is produced using DFR, the steps generally include film-bonding, lamination, exposure, and development to form a resist pattern on a substrate. After the resist pattern is formed, processes for forming a circuit can be roughly classified into two types, a via-capping method and a plating method. The via-capping method is a method of etching a bare copper surface on a copper-plated laminate not covered with a resist pattern, and then removing the resist pattern with a stripping solution more alkaline than a developing solution to leave the same wiring pattern as the resist pattern. The plating method is a method in which the bare copper surface of the copper-plated laminate not covered with the resist pattern is plated, the resist pattern is removed in the same manner as in the case of the via-capping method, and the bare copper surface after film removal is further etched, and the etching is generally performed with an acidic solution such as copper chloride or ferric chloride.
From the viewpoint of production process, adhesion property and etching resistance of the dry film resist are particularly important in the flow of resist and plating. In the via-capping method, it is necessary to have excellent adhesion between the resist and copper so that the etching solution does not penetrate between the resist film and the copper surface along the edge of the cured resist line. Once the etching solution infiltrates into the copper surface due to the loose and firm bonding between the resist and the copper surface, the resist line floats, which may result in the copper to be formed into the circuit portion being etched away, forming a narrow-top and wide-bottom circuit pattern, and even causing open circuit problem. In the plating method, in order to prevent the plating solution from penetrating between the resist and the copper surface, a burr-like or convex-like undesired solder pattern is formed at the edge of the plated wiring, which is a phenomenon of plating bleeding, in accordance with the via-capping method.
To produce narrow pitch patterns with higher yield, circuit board manufacturers have placed higher fundamental demands on dry film resist performance, high resolution, and high adhesion. From the viewpoint of producing a wiring pattern with higher production efficiency, a dry film resist is required to have characteristics such as a high developing speed and a short film removing time. In order to improve the adhesion of a dry film resist, it has been found that the etching resistance, plating resistance and coloring property are improved to some extent by using a monomer having a urethane structure (Japanese patent application laid-open No. 63-184744), but the resolution is insufficient.
Therefore, there is a need for a photosensitive resin composition with high adhesion and etching resistance, which has excellent resolution, good adhesion and etching resistance after being prepared into a photosensitive dry film resist, thereby improving the production efficiency and yield of CPB circuit boards.
Disclosure of Invention
The invention aims to make up the defects of the prior art and provides a high-adhesion etching-resistant photosensitive resin composition, and a dry film circuit prepared by coating the photosensitive resin composition after a photosensitive dry film resist is subjected to film pasting, exposure and development processes has excellent adhesion and good resolution on a metal plate used for a PCB.
The purpose of the invention is realized by the following technical scheme: the photosensitive resin composition mainly comprises 45-70 wt% of alkali-soluble copolymer resin with the weight-average molecular weight of 50,000-150,000, 15-45 wt% of olefinic photopolymerization unsaturated monomer, 1-10 wt% of photopolymerization initiator and 0.5-5 wt% of additive, wherein the alkali-soluble copolymer resin is prepared by polymerizing cycloolefine anhydride containing double six-membered ring rigid structure shown in a structural formula (I), (methyl) acrylic acid shown in a structural formula (II) and (methyl) acrylate free radical shown in a structural formula (III).
Further, the alkali-soluble copolymer resin has the following general formula (I)x(Ⅱ)y(Ⅲ)zWherein x, y and z respectively represent the specific gravity of I, II and III in alkali soluble resin, wherein x is 5-20 wt%, y is 20-35 wt% and z is 45-60 wt%.
Further, the acid value of the alkali-soluble copolymer resin is 110-200mg KOH/g resin, the weight average molecular weight is 50,000-150,000, and the molecular weight distribution is 1.3-2.5.
Further, the ethylenically photopolymerizable unsaturated monomer is composed of (meth) acrylate containing a bisphenol A structure; polyethylene glycol di (meth) acrylate; polypropylene glycol-based di (meth) acrylate; polyethylene oxide and propylene oxide-based di (meth) acrylate; alkyl (meth) acrylates; trimethylolpropane tri (meth) acrylate; alkoxylated trimethylolpropane triacrylate; pentaerythritol tri (meth) acrylate; alkoxylated pentaerythritol tri (meth) acrylate; pentaerythritol tetra (meth) acrylate; alkoxylated pentaerythritol tetra (meth) acrylate; dipentaerythritol tetra (meth) acrylate; alkoxylated dipentaerythritol tetra (meth) acrylate; nonylphenol (meth) acrylate; alkoxylated nonylphenol (meth) acrylates; phenoxyethyl (meth) acrylate; one or more of the alkoxylated phenoxyethyl (methyl) acrylate is mixed according to any proportion.
Further, the (meth) acrylate compound having a bisphenol a structure is selected from the group consisting of bisphenol a di (meth) acrylate, ethoxylated (propoxylated) bisphenol a dimethacrylate, and bisphenol a diglycidyl ether dimethacrylate, and is preferably bisphenol a di (meth) acrylate.
Further, the (meth) acrylate is preferably methyl methacrylate, ethyl acrylate, or butyl acrylate.
Further, the photopolymerization initiator is a hexaarylbisimidazole derivative.
Further, the photopolymerization initiator may be prepared from 2,2 ', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4', 5 '-diphenyl-1, 1' -diimidazole, 2- (o-chlorophenyl) -4, 5-diphenylimidazole dimer, one or more of 2- (o-chlorophenyl) -4, 5-bis (methoxyphenyl) imidazole dimer and 2- (o-fluorophenyl) -4, 5-diphenylimidazole dimer are mixed in an arbitrary ratio, and 2,2 ', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4', 5 '-diphenyl-1, 1' -diimidazole is more preferable.
Furthermore, the additive is formed by mixing one or more of light color former, color-forming heat stabilizer, plasticizer, antioxidant and deodorant according to any proportion.
The invention has the following beneficial effects: the invention can effectively enhance the binding capacity and the etching resistance to the substrate copper plate by introducing the anhydride with the rigid structure of the double six-membered ring into the alkali-soluble resin polymerization monomer, thereby reducing the phenomena of diffusion plating, short circuit and open circuit in the graphic process.
Detailed Description
The alkali soluble resin is one of the core components of the photosensitive resin composition, and the targeted addition of the functional monomer can significantly improve the comprehensive properties of the photosensitive resin composition, such as adhesion, development rate, storage stability, etching resistance and the like.
The present invention discloses a highly adhesive and etch resistant photosensitive resin composition, which is described in more detail below.
The present invention is also characterized by providing a high adhesion and etch resistant photosensitive resin composition having excellent adhesion to metal plates for PCB use, and characteristics of high developing rate and good resolution after development, etc. by introducing a functional monomer from the polymer main chain of an alkali-soluble resin and applying it to the photosensitive resin composition.
The following describes preferred embodiments of the present invention and comparative examples. However, the following embodiments are merely preferred embodiments of the present invention and do not limit the present invention.
1. Synthesis of anhydride TM containing double six-ring rigid Structure
Adding Maleic Anhydride (MA) into a four-neck flask provided with a thermometer, a stirring device, a dropping funnel and a condensing tube, stirring and heating to be molten, adding activated silica gel accounting for 6% of the weight of terpinene as a catalyst, heating to 140 ℃, dropwise adding terpinene, keeping the dropwise addition for about 2 hours until the dropwise addition is completed, wherein the dosage ratio of terpinene to maleic anhydride is 1.8:1, then heating to 150 ℃, keeping a constant temperature reaction for 2.5 hours, sampling, using N, N-dimethylaniline to check that no red color exists, namely the maleic anhydride is reacted, cooling to room temperature in a water bath, adding toluene to dilute reaction liquid, removing the catalyst by suction filtration, distilling out toluene and unreacted terpinene under reduced pressure, and collecting distillate under 190-200 ℃ (1.1-1.3 k Pa) to obtain the maleic anhydride (TM) containing a double six-ring rigid structure of an addition product.
2. The following alkali-soluble copolymer resin Z was synthesized.
Prepared by free radical solution polymerization, comprising the following steps:
uniformly mixing alkali-soluble copolymer monomers according to a certain mass ratio (total 100g), adding an initiator AIBN, adding 95g of butanone and 15g of ethanol, stirring for dissolving, adding a mixed solution with the mass fraction of about 35% into a three-neck flask with a nitrogen protection and condensation reflux device through a peristaltic pump, heating to 78 ℃ in an oil bath, stirring for reacting for 1h, slowly dropwise adding the rest mixed solution, and finishing adding within 3 h. And after the reaction is continued for 4 hours, heating to 90 ℃, supplementing 20g of butanone solution dissolved with 0.2g of initiator twice at an interval of 1 hour, stirring for 2 hours under heat preservation after the dropwise addition is finished, and finishing the reaction. The alkali-soluble copolymer resin was obtained, and its weight-average molecular weight, molecular weight distribution and solid content were measured by GPC.
3. Preparation of photosensitive resin composition
The photosensitive resin composition of the present invention contains an additive in addition to the alkali-soluble copolymer resin, the ethylenically photopolymerizable unsaturated monomer, and the photopolymerization initiator, wherein the additive is prepared by mixing one or more of a light coupler, a color-forming heat stabilizer, a plasticizer, an antioxidant, and a deodorant at any ratio. The light color former can adopt one or more of diamond green GH, leuco crystal violet, tribromomethylphenyl sulfone, methyl orange, basic green 1, basic green 2, basic green 3, basic green 4, basic green 5, phthalocyanine blue and rhodamine B; the color-forming heat stabilizer can be one or more of methoxyphenol, hydroquinone, alkyl or aryl substituted hydroquinone, benzoquinone, tert-butyl catechol, pyrogallol, copper resin, beta-phenolic acid, 2, 4-di-tert-butyl-p-cresol, 2-methenyl-bis (4-ethyl-6-tert-butyl-phenol), p-toluquinone, tetrahydro-p-benzoquinone and aryl phosphite; the plasticizer can adopt one or more of benzotriazole, di (2-ethylhexyl) phthalate, dibutyl phthalate, tributyl citrate and acetyl tributyl citrate; the antioxidant can be one or more of octadecyl propionate, 2, 6-di-tert-butyl-p-cresol, dilauryl thiodipropionate and trisnonylphenyl phosphite; the deodorant may be one or more of hydrogenated polyprenol, eugenol, polyoxyethylene lauryl (dodecyl) ether, and sodium diisooctyl sulfosuccinate, but is not limited thereto.
A series of alkali-soluble resins Z-1 to Z-5 were synthesized according to the formulation of Table 1 below
Table 1: alkali soluble resin Z-1-Z-5 component table
According to the formulation shown in the following table 2, the components are mixed according to the proportion, a certain amount of butanone and ethanol are added, and the mixture is fully stirred until the components are completely dissolved, so that the photosensitive resin composition with the solid content of 40% is prepared.
Table 2: ingredient list of photosensitive resin composition
4. A photosensitive dry film resist was prepared, and the photosensitive resin composition solution prepared in Table 2 was coated on a 15 μm PET film using a coater with selecting an appropriate wire bar and coating speed, and placed in an oven to dry for 8 min. After cooling, a PE film having a thickness of 18 μm was thermally laminated at a certain pressure and temperature using a hot rubber roller, thereby obtaining a dry film resist having a layer thickness of the photosensitive resin composition of 38 μm.
Test examples and comparative examples:
examples 1-10 and comparative examples 1-3 were used to evaluate adhesion and resolution using a 38 μm thick photosensitive resin.
[ film pasting ]: and polishing the copper surface of the copper-clad plate by a grinder, washing with water, and wiping to obtain a bright and fresh copper surface. The press roll temperature of the laminator is set to be 110 ℃, the conveying speed is 1.5m/min, and the hot lamination is carried out under the standard pressure.
[ Exposure ]: exposure was carried out using a Saint technologies model M-552 exposure machine and photosensitivity test was carried out using a stouffer 21 grid exposure ruler.
[ DEVELOPING ]: gradually increasing the line width/line distance of the film selected by developing from 10um to 100 um; the developing solution is 1 wt% sodium carbonate aqueous solution, the developing temperature is 30 deg.C, the developing pressure is 1.8bar, the developing speed is 1.5m/min, and the model of the developing machine is Yunsu science XY-430. The minimum time required for the resist layer of the unexposed portion to be completely dissolved is taken as the minimum development time.
[ resolution evaluation ]: the exposure was performed using a mask having a wiring pattern with a width of 1:1 of the exposed portion and the unexposed portion, and after development with 1.5 times of the minimum development time, the minimum mask width where the cured resist line was normally formed was taken as the value of the resolution.
[ evaluation of adhesion force ]: a photosensitive dry film resist was laminated on a copper plate by hot-pressing a film, exposed to light using a mask having a wiring pattern with a width of n:400 of an exposed portion and an unexposed portion, and developed with 1.5 times of the minimum development time, and then the minimum mask width where a cured resist line was normally formed was taken as a value of adhesion.
[ evaluation of adhesion after etching ]: carrying out an etching process on the developed copper plate, wherein an etching solution is copper chloride, the etching speed is 2.2m/min, the etching temperature is 48 ℃, the spray pressure is 1.5bar, the specific gravity is 1.3g/mL, the acidity is 2mol/L, the copper ions are 140g/L, and the type of an etching machine is DF-JYD 300; the minimum mask width of the cured resist line was taken as a value of the post-etching adhesion.
[ evaluation results ]
The evaluation results of the examples and comparative examples are shown in table 3.
Table 3: evaluation results table
It is apparent from examples 1 to 10 and comparative examples 1 to 3 that the adhesion of the dry films of examples 1 to 10 is reduced to a lower extent after undergoing an etching process, compared to the dry films prepared from an alkali-soluble acrylic resin to which the structural unit of the cycloolefin anhydride of a double six-membered ring rigid structure is not added, i.e., a pure acrylate resin (comparative examples 1 to 3). The adhesion of the examples 6 and 7 and the other 8 examples after etching was reduced by 5 μm and 0-3 μm, respectively, and the comparison result shows that the etching resistance of the dry film is continuously improved as the content of the cycloolefin anhydride TM in the double six-ring rigid structure is increased. As shown in comparative examples 1-4, the resin content can significantly affect the resolution and adhesion of the dry film, and the resolution and adhesion can reach the optimum values of 30 μm and 35 μm when the resin content is about 62%. It is clear from comparative examples 5, 9 and 10 that the low molecular weight of the alkali-soluble resin results in the decrease of the adhesion property, and the high molecular weight results in the poor resolution property. In summary, the present invention can provide a highly adhesive etching-resistant photosensitive resin composition, and the photosensitive dry film resist prepared by the composition can further improve the production efficiency and yield of PCBs in the actual production and application processes.
Claims (11)
1. The photosensitive resin composition is characterized by mainly comprising 45-70 wt% of alkali-soluble copolymer resin with the weight-average molecular weight of 50,000-150,000, 15-45 wt% of olefinic photopolymerization unsaturated monomer, 1-10 wt% of photopolymerization initiator and 0.5-5 wt% of additive, wherein the alkali-soluble copolymer resin is prepared by polymerizing cycloolefine acid anhydride containing a double six-membered ring rigid structure shown in a structural formula (I), (methyl) acrylic acid shown in a structural formula (II) and (methyl) acrylate free radicals shown in a structural formula (III);
2. The highly adhesive etching-resistant photosensitive resin composition according to claim 1, wherein the alkali-soluble copolymer resin has the following general formula (I)x(Ⅱ)y(Ⅲ)zWherein x, y and z respectively represent the specific gravity of I, II and III in alkali soluble resin, wherein x is 5-20 wt%, y is 20-35 wt% and z is 45-60 wt%.
3. The highly adhesive etching-resistant photosensitive resin composition as claimed in claim 1, wherein the alkali-soluble copolymer resin has an acid value of 110-200mg KOH/g resin, a weight average molecular weight of 50,000-150,000, and a molecular weight distribution of 1.3-2.5.
4. The highly adhesive etching-resistant photosensitive resin composition according to claim 1, wherein the ethylenically photopolymerizable unsaturated monomer is selected from the group consisting of (meth) acrylates containing a bisphenol A structure; polyethylene glycol di (meth) acrylate; polypropylene glycol-based di (meth) acrylate; polyethylene oxide and propylene oxide-based di (meth) acrylate; alkyl (meth) acrylates; trimethylolpropane tri (meth) acrylate; alkoxylated trimethylolpropane triacrylate; pentaerythritol tri (meth) acrylate; alkoxylated pentaerythritol tri (meth) acrylate; pentaerythritol tetra (meth) acrylate; alkoxylated pentaerythritol tetra (meth) acrylate; dipentaerythritol tetra (meth) acrylate; alkoxylated dipentaerythritol tetra (meth) acrylate; nonylphenol (meth) acrylate; alkoxylated nonylphenol (meth) acrylates; phenoxyethyl (meth) acrylate; one or more of the alkoxylated phenoxyethyl (methyl) acrylate is mixed according to any proportion.
5. The photosensitive resin composition of claim 4, wherein the (meth) acrylate compound having a bisphenol A structure in the ethylenically photopolymerizable unsaturated monomer is selected from the group consisting of bisphenol A di (meth) acrylate, ethoxylated (propoxylated) bisphenol A dimethacrylate, and bisphenol A diglycidyl ether dimethacrylate.
6. The highly adhesive etching-resistant photosensitive resin composition according to claim 5, wherein the (meth) acrylate compound having a bisphenol A structure is bisphenol A di (meth) acrylate.
7. The highly adherent, etch resistant photosensitive resin composition of claim 1, wherein the (meth) acrylate is selected from the group consisting of methyl methacrylate, ethyl acrylate, butyl acrylate.
8. The highly adhesive etching-resistant photosensitive resin composition according to claim 1, wherein the photopolymerization initiator is a hexaarylbisimidazole derivative.
9. The highly adhesive etching-resistant photosensitive resin composition according to claim 8, wherein the photopolymerization initiator is composed of one or more selected from the group consisting of 2,2 ', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4', 5 '-diphenyl-1, 1' -diimidazole, 2- (o-chlorophenyl) -4, 5-diphenylimidazole dimer, 2- (o-chlorophenyl) -4, 5-bis (methoxyphenyl) imidazole dimer, and 2- (o-fluorophenyl) -4, 5-diphenylimidazole dimer, which are mixed in an arbitrary ratio.
10. The photosensitive resin composition of claim 9, wherein the photopolymerization initiator is 2,2 ', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4', 5 '-diphenyl-1, 1' -diimidazole.
11. The highly adhesive etching-resistant photosensitive resin composition according to claim 1, wherein the additive is a mixture of one or more of a photo-coupler, a color-forming heat stabilizer, a plasticizer, an antioxidant and a deodorant in any ratio.
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| CN101952778A (en) * | 2008-01-24 | 2011-01-19 | 旭化成电子材料株式会社 | Photosensitive resin laminate |
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