KR20140147526A - Photosensitive Resin Composition and Dry Film Photoresist Formed Thereof - Google Patents
Photosensitive Resin Composition and Dry Film Photoresist Formed Thereof Download PDFInfo
- Publication number
- KR20140147526A KR20140147526A KR20130070949A KR20130070949A KR20140147526A KR 20140147526 A KR20140147526 A KR 20140147526A KR 20130070949 A KR20130070949 A KR 20130070949A KR 20130070949 A KR20130070949 A KR 20130070949A KR 20140147526 A KR20140147526 A KR 20140147526A
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- South Korea
- Prior art keywords
- resin composition
- photosensitive resin
- meth
- acrylate
- weight
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
Abstract
Description
The present invention relates to a photosensitive resin composition and a dry film photoresist prepared therefrom.
Generally, dry film photoresists are widely used for lamination on copper clad laminates. In this regard, an example of a manufacturing process of a printed circuit board (hereinafter referred to as a PCB) is a preprocessing process in order to laminate a copper clad laminate as a raw material of a PCB. The pretreatment process is in the order of drilling, deburring, and frontal in the outer layer process, and is faced or pickled in the inner layer process. Bristle brush and jet pumice process are mainly used in the frontal process, and pickling can be performed by soft etching and 5 wt% sulfuric acid pickling.
In order to form a circuit on the copper-clad laminate after the pretreatment, a dry film photoresist (hereinafter referred to as DFR) is usually laminated on the copper layer of the copper clad laminate. In this process, the photoresist layer of the DFR is laminated on the copper surface while removing the protective film of the DFR using a laminator. Generally, the lamination speed is 0.5 to 3.5 m / min, the temperature is 100 to 130 캜, and the roller pressure is 10 to 90 psi.
The laminated printed circuit board is exposed to the photoresist of the DFR using a photomask having a desired circuit pattern after being left for 15 minutes or more for stabilizing the substrate. When the ultraviolet rays are irradiated to the photomask in this process, the photoresist irradiated with ultraviolet light starts to be polymerized by the photoinitiator contained in the irradiated site. Initially, the oxygen in the photoresist is consumed, and the next activated monomer is polymerized to initiate a crosslinking reaction, and then a large amount of monomer is consumed and polymerization proceeds. On the other hand, the unexposed portion exists in a state in which the crosslinking reaction does not proceed.
Next, a developing process for removing the unexposed portions of the photoresist is carried out. In the case of the alkali developing DFR, 0.8 to 1.2% by weight of potassium carbonate and aqueous solution of sodium carbonate are used as a developing solution. In this process, the photoresist of the unexposed portion is washed away by the saponification reaction between the carboxylic acid of the binder polymer and the developer in the developer, and the cured photoresist remains on the copper surface.
The circuit is then formed through other processes depending on the inner and outer layer processes. In the inner layer process, a circuit is formed on the substrate through the etching and peeling process. In the outer layer process, the plating and the tentering process are performed, and etching and solder peeling are performed to form a predetermined circuit.
In general, the dry film photoresist exposed in the plating process is placed in a strong acid or strong alkaline solution environment. For this reason, when the chemical resistance is insufficient, the dry film photoresist is separated from the copper clad laminate.
The main object of the present invention is to provide a photosensitive resin composition having improved chemical resistance while exhibiting inherent physical properties such as fine line adhesion and resolution in a dry film photoresist, and a dry film photoresist prepared using the photosensitive resin composition.
In order to achieve the above object, one embodiment of the present invention relates to a photopolymerizable oligomer; A photopolymerization initiator; And a binder polymer, wherein the photopolymerizable oligomer comprises a compound represented by the general formula (1).
≪ Formula 1 >
In the above formula (1), 1 + p is 10 to 30 and n + o is 3 to 10.
In one preferred embodiment of the present invention, the compound represented by Formula 1 may include 0.1 to 60% by weight based on the total weight of the solid content of the photosensitive resin composition .
In one preferred embodiment of the present invention, the photosensitive resin composition comprises 0.1 to 70% by weight of a photopolymerizable oligomer, 1 to 25% by weight of a photopolymerization initiator and 20 to 80% by weight of a binder polymer, based on the total solid content of the photosensitive resin composition . ≪ / RTI >
In one preferred embodiment of the present invention, the photopolymerizable oligomer further comprises a monomer having at least two ethylene groups at the terminal.
In one preferred embodiment of the present invention, the monomer having at least two ethylene groups at the terminal is selected from 1,6-hexanediol (meth) acrylate, 1,4-cyclohexanediol- (meth) acrylate, polyethylene glycol di Methacrylate, trimethylolpropane triacrylate, polypropylene glycol- (meth) acrylate, poly-ethylene glycol- (meth) acrylate, 2-di- (p- (Meth) acrylate, glycerol tri (meth) acrylate, trimethylol propane tri- (meth) acrylate, 2,2'-bis- [4- (methacryloxy-polyethoxy) (Meth) acrylate containing a bisphenol A group, polyfunctional (meth) acrylate containing a urethane group and at least one member selected from the group consisting of (meth) acrylate, include That may be characterized.
In one preferred embodiment of the present invention, the monomer having at least two ethylene groups at the terminal may be contained in an amount of 20 to 80% by weight based on the total weight of the solid content of the photopolymerizable oligomer.
Another embodiment of the present invention provides a dry film photoresist comprising a photoresist layer formed from the photosensitive resin composition.
The photosensitive resin composition according to the present invention and the dry film photoresist produced therefrom have excellent chemical resistance while exhibiting inherent physical properties such as fine line adhesion and resolution and are stable to plating and etching processes, It is possible to make the board of the form easily.
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In general, the nomenclature used herein is well known and commonly used in the art.
Throughout this specification, when an element is referred to as "including " an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise.
In one aspect, the present invention relates to a photopolymerizable oligomer; A photopolymerization initiator; And a binder polymer, wherein the photopolymerizable oligomer comprises a compound represented by the general formula (1).
≪ Formula 1 >
In the above formula (1), 1 + p is 10 to 30, and n + o is 3 to 10.
Hereinafter, the present invention will be described in more detail.
(1) Photopolymerizable oligomer
The photopolymerizable oligomer of the present invention includes a compound represented by the following formula (1) containing a bisphenol compound and propylene oxide.
≪ Formula 1 >
In the formula 1, 1 + p is 10 to 30, n + o is 3 to 10, and l + p is preferably 10 to 15 in terms of workability and resolution, and n + o may be 3 to 5 . If l + p is less than 10, or n + o is less than 3, an operation problem such as lowering of the developing speed may occur. If l + p exceeds 30 or n + The resolution may be lowered.
The compound represented by the formula (1) according to the present invention contains a bisphenol compound in its structure and can increase the chemical resistance. By containing the propylene oxide having controlled chain number, the compound can be improved in hydrophobicity, The resistance can be remarkably increased.
The compound represented by Formula 1 is preferably contained in an amount of 0.1 to 60% by weight based on the total weight of the solid content of the photosensitive resin composition, and more preferably 0.5 to 50% by weight in view of resolution and chemical resistance. If the compound represented by the general formula (1) is contained in an amount of more than 60% by weight based on the total weight of the solid content of the photosensitive resin composition, the hydrophobicity of the compound increases and the development time in the development step after exposure tends to increase sharply If it is less than 0.1% by weight, the effect on addition of the compound represented by the formula (1) may be insignificant.
In addition, the photopolymerizable oligomer of the present invention may further include a monomer having at least two ethylene groups at the terminal thereof in addition to the compound represented by the above-mentioned formula (1) in terms of adhesion and resolution in terms of fine lines. Examples thereof include 1,6- (Meth) acrylate, polypropylene glycol (meth) acrylate, poly (ethylene glycol) -methyl (meth) acrylate, 1,4-cyclohexanediol-methacrylate, polyethylene glycol dimethacrylate, trimethylolpropane triacrylate, (Meth) acrylate, 2-di- (p-hydroxyphenyl) -propane-di- (meth) acrylate, glycerol tri (meth) acrylate, trimethylolpropane tri- (Propylene) di (meth) acrylate containing a bisphenol A group, poly (meth) acrylates such as 2'-bis- [4- (methacryloxy-polyethoxy) phenyl] propane, polyoxypropyl trimethylolpropane tri Sites, and the like can be a multi-functional (meth) acrylate containing urethane groups.
The content of the monomer having at least two ethylene groups at the terminal is preferably 20 to 80% by weight based on the total weight of the photopolymerizable oligomer from the viewpoint of fine line adhesion and resolution.
The content of the photopolymerizable oligomer is preferably 0.1 to 70% by weight based on the total weight of the solid content of the photosensitive resin composition in terms of excellent chemical resistance while exhibiting inherent properties such as fine line adhesion and resolution.
(2) Photopolymerization initiator
In the photosensitive resin composition of the present invention, the photopolymerization initiator is a compound that initiates a chain reaction with the photopolymerizable oligomer by ultraviolet (UV) and other radiation, and is a compound that plays an important role in the curing of the dry film resist.
Examples of such photopolymerization initiator compounds include anthraquinone derivatives such as 2-methyl anthraquinone and 2-ethyl anthraquinone; And benzoin derivatives such as benzoin methyl ether, benzophenone, phenanthrenequinone, and 4,4 'bis- (dimethylamino) benzophenone.
In addition to these, there may be mentioned 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenylethan-1-one, 2-methyl- 1- [4- (methylthio) 1-one, 2-benzyl-2-dimethylamino-1- [4-morpholinophenyl] butan- 2-methylpropan-1-one, 2,4-diethyl (2-hydroxyethyl) 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 3,3-dimethyl-4-methoxybenzophenone, benzophenone, 1-chloro-4- (4-isopropylphenyl) 2-hydroxy-2-methylpropan-1-one, 1- Dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, butyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2-isoamyl 4-dimethylaminobenzoate, 2,2-diethoxyacetophenone, benzylketone dimethyl acetal, benzyl ketone? -Methoxydiethyl acetal, 1-phenyl-1,2-propyldioxime-o methyl o-benzoyl benzoate, bis [4-dimethylaminophenyl) ketone, 4,4'-bis (diethylamino) benzophenone, 4,4'- Benzoin, methoxybenzoin, ethoxybenzoin, isopropoxybenzoin, n-butoxybenzoin, isobutoxybenzoin, tert-butoxybenzoin, p-dimethylaminoacetophenone , p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, thioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, dibenzosuberone, 4-phenoxyacetophenone, and pentyl 4-dimethylaminobenzoate.
The content of the photopolymerization initiator is usually 1 to 25% by weight based on the total weight of the solid content of the photosensitive resin composition. If the content of the photopolymerization initiator is less than 1% by weight based on the total weight of the solid content of the photosensitive resin composition, photo-crosslinking may not be performed properly. If the amount exceeds 25% by weight, photo- Or more.
(3) Binder polymer
In the photosensitive resin composition of the present invention, the binder polymer is an alkali-soluble polymer resin as a copolymer of (meth) acrylic acid and (meth) acrylic acid ester.
Examples of the copolymer of (meth) acrylic acid and (meth) acrylic acid ester include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, acrylic acid, methacrylic acid, methyl Methacrylic acid, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, acrylamide, methacrylamide, styrene, Methyl styrene, and the like.
These copolymers preferably have a weight average molecular weight of 30,000 to 150,000 g / mol and a glass transition temperature of 20 to 150 DEG C in consideration of the coating property and followability of the dry film resist and the mechanical strength of the resist itself after formation of the circuit Do. The weight average molecular weight was measured using a Waters 450 GPC, column styrene gel HR 4E X2, and styragel HR 5E X1 using THF as a mobile phase. The polystyrene was measured with a standard and measured at -30 ° C to 200 ° C using a Perkinelmer Diamond DSC The glass transition temperature was measured while raising the temperature at 10 캜 / min.
The content of the binder polymer is usually preferably 20 to 80% by weight based on the total weight of the solid content of the photosensitive resin composition. If the binder polymer is added in an amount of less than 20% by weight based on the total solid content of the photosensitive resin composition, the adhesion of the film can be greatly increased. If the binder polymer is added in an amount exceeding 80% by weight, ) May be generated.
(4) solvents and additives
The photosensitive resin composition of the present invention may contain a dye such as diamond green, a coloring agent such as tribromophenylsulfone, leuco crystal violet and the like depending on an optional purpose, and the content thereof is preferably 0.01 to 10% by weight of the solid content of the entire photosensitive resin composition Is usually preferred.
In addition, the photosensitive resin composition may contain the solvent by suitably adjusting it according to the purpose. Examples of the solvent include methyl ethyl ketone (MEK), tetrahydrofuran (THF), methanol, ethanol, acetone, and toluene.
In addition, the photosensitive resin composition makes it possible to distinguish exposure from unexposed light by changing the unoccluded light to green and the exposed part to blue by adding a dye. The photosensitive resin composition may further optionally include a plasticizer, a leveling agent, a heat stabilizer, and an additive for long-term storage stability.
In another aspect, the present invention relates to a dry film photoresist prepared using the photosensitive resin composition.
The dry film photoresist according to the present invention can be obtained by coating the above-mentioned photosensitive resin composition on at least one surface of a base film such as polyethylene terephthalate to form a photosensitive layer (photoresist layer) with a thickness of 5 to 200 μm. At this time, the method of forming the photosensitive layer (photoresist layer) can be generally used without particular limitation, as long as the photosensitive layer can be formed using a resin composition.
The polymeric binder, the photopolymerizable polyfunctional monomer, the photopolymerization initiator, and the like described above are not intended to limit the present invention, and those skilled in the art will understand that various compounds Of course.
Hereinafter, preferred embodiments and comparative examples of the present invention will be described. However, the following embodiments are merely preferred embodiments of the present invention, and the present invention is not limited to the following embodiments.
< Example 1>
The photopolymerizable oligomer (PDBPE-0412, Japan) obtained in Production Example 1, the photopolymerization initiator, the binder polymer and the additive were adjusted to have compositions as shown in Table 1, coated on the polyethylene terephthalate film, and dried at room temperature Thereby forming a photosensitive layer having a thickness of 30 mu m. Thereafter, a polyethylene film was laminated on the photosensitive layer with a protective film to prepare a dry film photoresist. The content in Table 1 means the weight percentage contained in the solid content of the photosensitive resin composition.
The dry film photoresist prepared using the photosensitive resin composition prepared above was subjected to the following steps.
< Lamination >
The dry film photoresist was polished to a brush-polished copper-clad laminate having a thickness of 1.6 mm, a substrate preheating roll temperature of 120 캜, a laminator roll temperature of 115 캜, a roll pressure of 4.0 kgf / cm 2 And laminated using a HAKUTO MACH 610i under a roll speed of 2.5 min / m.
<Phenomenon and resolution>
The dry film photoresist laminated on the copper-clad laminate was irradiated with ultraviolet rays at an exposure dose of 40 mJ using a Perkin-Elmer ( TM) OB7120 (parallel light exposing machine) using a circuit evaluation photomask, and left for 20 minutes. Thereafter, the development was carried out under the development conditions of spraying method with a 1.0 wt% aqueous solution of Na 2 CO 3 . The time taken until the dry film photoresist on the copper foil laminates was completely washed in the developing solution was measured using a stopwatch (minimum development time), and the product was fixed at a break point of 50% (minimum development time 2 ship).
< Example 2 to 4 and Comparative Example 1 and 2>
The photosensitive composition was prepared in the same manner as in Example 1 except for the content and the content of the photopolymerizable oligomer, and a dry film photoresist was prepared. The components and contents of the photopolymerizable oligomers used in Examples 2 to 4 and Comparative Examples 1 and 2 are shown in Table 2 below. The content in the following Table 2 means the weight percentage contained in the solid content of the photosensitive resin composition.
The properties of the dry film photoresist prepared using the photosensitive resin compositions prepared in Examples 1 to 4 and Comparative Examples 1 and 2 were measured by the following methods, and the results are shown in Table 3 below.
≪ Development time (unit: second) >
As described above, the time required for the dry film photoresist at the unexposed portion on the copper-clad laminate to be completely washed in the developing solution after the development was measured using a stopwatch (minimum developing time) And fixed at 50% (twice the minimum developing time).
≪ Fine wire adhesion (unit: 占 퐉)
After development, the ZEISS AXIOPHOT Microscope was used to measure the minimum line width at which the independent resist survives.
<Resolution (unit: 탆)>
The space between the circuit line and the circuit line was measured at 1: 1 and measured with a ZEISS AXIOPHOT Microscope.
<Tolerance of borohydric acid (unit: minute)>
After the development process, the copper clad laminate was deeply dipped in borofluoric acid commonly used in the relevant industry to evaluate chemical resistance. After immersing in borofluoric acid, the film was taken out every 10 minutes to confirm that the dry film photoresist adhered to the copper-clad laminate. That is, the time when the thin line having a line width of 100 mu m is attached is measured and measured. The method of confirming was that high-pressure air was sprayed on a line width of 100 mu m to visually confirm the detachment of the resist.
* 1 Development time is 50% of break point.
* 2 The fine line adhesion is the minimum line width in which the independent line width survives after development.
* 3 Resolution is measured with a 1: 1 space between the circuit line and the circuit line.
* 4 Borophosphoric acid tolerance: The time when the thin line with a line width of 100 μm is attached.
As shown in Table 3, it can be seen that Examples 1 to 4 are remarkably superior in chemical resistance to borofluoric acid while maintaining the same level of fine line adhesion and resolution as Comparative Example 1. It is also understood that Examples 1 to 4 are significantly faster in developing time than Comparative Example 2.
It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (7)
≪ Formula 1 >
In Formula 1, 1 + p is 10 to 30, and n + o is 3 to 10.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20130070949A KR20140147526A (en) | 2013-06-20 | 2013-06-20 | Photosensitive Resin Composition and Dry Film Photoresist Formed Thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| KR20130070949A KR20140147526A (en) | 2013-06-20 | 2013-06-20 | Photosensitive Resin Composition and Dry Film Photoresist Formed Thereof |
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| KR20140147526A true KR20140147526A (en) | 2014-12-30 |
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| KR20130070949A KR20140147526A (en) | 2013-06-20 | 2013-06-20 | Photosensitive Resin Composition and Dry Film Photoresist Formed Thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180072835A1 (en) * | 2015-03-19 | 2018-03-15 | Hitachi, Ltd. | Immobilization carrier, polyether compound used for producing same and method for producing immobilization carrier |
| KR20180044925A (en) * | 2015-08-21 | 2018-05-03 | 도아고세이가부시키가이샤 | Curable composition |
-
2013
- 2013-06-20 KR KR20130070949A patent/KR20140147526A/en not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180072835A1 (en) * | 2015-03-19 | 2018-03-15 | Hitachi, Ltd. | Immobilization carrier, polyether compound used for producing same and method for producing immobilization carrier |
| US10633475B2 (en) * | 2015-03-19 | 2020-04-28 | Hitachi, Ltd. | Immobilizing carrier, polyether compound used for producing same and method for producing immobilization carrier |
| KR20180044925A (en) * | 2015-08-21 | 2018-05-03 | 도아고세이가부시키가이샤 | Curable composition |
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