KR20140087164A - Photosensitive Resin Composition for Dry Film Photoresist - Google Patents
Photosensitive Resin Composition for Dry Film Photoresist Download PDFInfo
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- KR20140087164A KR20140087164A KR1020120155793A KR20120155793A KR20140087164A KR 20140087164 A KR20140087164 A KR 20140087164A KR 1020120155793 A KR1020120155793 A KR 1020120155793A KR 20120155793 A KR20120155793 A KR 20120155793A KR 20140087164 A KR20140087164 A KR 20140087164A
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- photosensitive resin
- resin composition
- dry film
- film photoresist
- 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
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
The present invention relates to a photosensitive resin composition for a dry film photoresist.
The photosensitive resin composition is used in the form of a dry film photoresist (DFR) or a liquid photoresist ink used for a printed circuit board (PCB) or a lead frame have.
In addition to the production of printed circuit boards (PCBs) and lead frames, Rib barriers for plasma display panels (PDPs), ITO electrodes for other displays, bus address electrodes, and (Black Matrix) Dry film photoresists are widely used.
In manufacturing a printed circuit board, a lead frame and the like, one of the most important processes is a process of forming circuits such as a copper clad lamination sheet (CCLS) and a copper foil. The image transfer method used in this process is called photolithography and the original image plate used for this photolithography is called Artwork (commonly used terms in the PCB and the lead frame manufacturing part) and Photomask Quot;). ≪ / RTI >
Then, the portion of the artwork image where the light passes and the portion that does not pass through the image are transferred, and the image is transferred using the portion. This image transfer process is called an exposure process.
The image of such an artwork is transferred to CCLS or copper foil by light transmission and non-penetration. At this time, the photoresist (hereinafter referred to as PR) is the material that forms the image by receiving the light. Therefore, PR must be laminated or coated on CCLS, copper foil, etc. before transferring the image of the artwork.
In the exposure process, typically, PCB and lead frame makers are exposed to ultraviolet rays (UV) containing i-line (365 nm) emitted by a high-pressure mercury lamp to polymerize and cure the exposed portions. In recent years, direct drawing by laser, that is, maskless exposure which does not require artwork, has been rapidly diffused. As a light source for maskless exposure, light with a wavelength of 350 to 410 nm, particularly i-line (365 nm) or h-line (405 nm) is often used. However, compared with the conventional ultra high-pressure mercury lamp exposure, maskless exposure requires a high-sensitivity PR that shortens the exposure time because of a long exposure time.
The main object of the present invention is to provide a photosensitive resin composition for a dry film photoresist which is capable of securing excellent resolution and fine line adhesion even at a low exposure dose by improving the sensitivity of the photosensitive resin composition and is particularly suitable for a laser direct exposure machine.
In order to achieve the above object, the present invention provides a photopolymerizable composition comprising, in one embodiment, [A] a photopolymerization initiator, [B] an alkali developable binder polymer and a photopolymerizable compound having an ethylenically unsaturated bond in the [C] ] The photosensitive resin composition for a dry film photoresist according to claim 1, wherein the photopolymerization initiator comprises a compound represented by the following general formula (1).
[Chemical Formula 1]
In one preferred embodiment of the present invention, the photosensitive resin composition comprises 0.5 to 20% by weight of [A] a photopolymerization initiator, 40 to 70% by weight of an alkali developable binder polymer, and 10 to 50% by weight of a [C] And a control unit.
In one preferred embodiment of the present invention, the compound represented by Formula 1 may include 0.1 to 2% by weight based on the total weight of the photosensitive resin composition.
In a preferred embodiment of the present invention, the photosensitive resin composition is exposed by a laser direct exposure machine to cure the exposed portion, and a resist pattern is formed by a developing process.
According to the present invention, it is possible to improve the sensitivity of the photosensitive resin composition for a dry film photoresist to ensure appropriate physical properties (resolution, fine wire adhesion, etc.) even at a low exposure dose, and also to a laser direct exposure machine, There is an effect that productivity can be maximized in generating an image in a company that controls the display device, a PCB, a lead frame, a PDP, and other display devices.
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.
The present invention relates to a photocurable composition comprising a photopolymerization initiator [A], an alkali developable binder polymer, and a [C] photopolymerizable compound, wherein the [A] photopolymerization initiator comprises a compound represented by the following formula To a photosensitive resin composition for a film photoresist.
[Chemical Formula 1]
The present invention relates to a photosensitive resin composition for a dry film photoresist which can improve the sensitivity of a photosensitive resin composition and ensure appropriate physical properties (resolution, fine wire adhesion, etc.) even at a low exposure dose and can be suitably used in a laser direct- .
The photosensitive resin composition for a dry film photoresist according to the present invention preferably contains a compound represented by the general formula (1) as the [A] photopolymerization initiator. The compound represented by the above formula (1) can increase the sensitivity of the photosensitive resin composition to laser direct exposure and ensure proper physical properties even at a low exposure dose.
The photosensitive resin composition for a dry film photoresist according to the present invention reacts extremely sensitively to light and can sufficiently form a reaction by using only a small amount of exposure energy and can form a circuit. The compound represented by the general formula (1) A good circuit can be formed during various steps of resist pattern formation, and the exposure time is shortened even with a small amount of exposure energy, thereby maximizing productivity in generating an image.
Hereinafter, the present invention will be described in more detail.
[A] Photopolymerization initiator
The photopolymerization initiator contained in the photosensitive resin composition for a dry film photoresist of the present invention is a substance that initiates a chain reaction of a photopolymerizable monomer by UV and other radiation and plays an important role in curing the dry film photoresist.
In the present invention, the photopolymerization initiator includes the compound represented by the above formula (1). Since the compound represented by Formula 1 reacts sensitively to UV, sufficient photoreaction can be achieved even with a small exposure energy, thereby increasing sensitivity to laser direct exposure and improving resistance to a developing solution in a developing process to form a good circuit .
The content of the compound represented by the general formula (1) serving as such is preferably in the range of If the content of the initiator is less than 0.1% by weight, the reactivity of the initiator becomes weak, so that it can not be used at a low exposure energy amount (about 30 mJ / cm 2 ). If the content is more than 2% by weight, It is impossible to realize a desired circuit width after the etching process. In severe cases, open failure may be caused.
The photopolymerization initiator may further include a photopolymerization initiator that is commonly used in addition to the compound represented by the general formula (1).
The commonly used photopolymerization initiators include 2,2'-bis (2-chlorophenyl) -4,4'-5,5'-tetraphenylbisimidazole, 1-hydroxycyclohexylphenylketone, 2,2'- 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, 2-benzyl- Amino-1- [4-morpholinophenyl) butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2-methylpropan-1-one, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4- -Dimethylthioxanthone, 3,3-dimethyl-4-methoxybenzophenone, benzophenone, 1-chloro-4-propoxyoxanthone and 1- (4-isopropylphenyl) 2-methylpropan-1-one, 4-benzoyl-4'-methyldimethylsulfide, 4-dimethylaminobenzoic acid, methyl 4 - dimethylaminobenzoate, ethyl 4-dimethylamino Dimethyl aminobenzoate, 2-isoamyl 4-dimethylaminobenzoate, 2,2-diethoxyacetophenone, benzyl ketone dimethyl acetal, benzyl ketone beta Benzoyl benzoate, bis [4-dimethylaminophenyl) ketone (hereinafter, referred to as " , 4,4'-bis (diethylamino) benzophenone, 4,4'-dichlorobenzophenone, benzyl, benzoin, methoxybenzoin, ethoxybenzoin, isopropoxybenzoin, n-butoxybenzo Butoxybenzoin, p-dimethylaminoacetophenone, p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, thioxanthone, 2-methylthioxanthone , 2-isopropylthioxanthone, dibenzosuberone,? -? - dichloro-4-phenoxyacetophenone, pentyl 4-dimethylaminobenzoate, 9-phenylacridine, But are not limited to, lysine, acridine compounds, thioxanthone compounds, anthracene compounds, coumarin compounds, pyrazoline compounds, hexaaryl-imidazole dimers, and the like .
The content of the photopolymerization initiator is in the range of 0.5 to 20% by weight in the photosensitive resin composition. When the content of the photopolymerization initiator is within the above range, sufficient sensitivity can be obtained.
[B] Alkali developing binder polymer
The alkali developable binder polymer of the present invention is a copolymer of (meth) acrylic acid and (meth) acrylic acid ester. Specific examples of the monomer include methyl acrylate, methyl methacrylate, ethyl acrylate, methyl methacrylate, butyl acrylate, butyl methacrylate, acrylic acid, methacrylic acid, 2-hydroxyethyl acrylate, 2- The copolymerization of two or more monomers selected from linear acrylic acid polymers synthesized from methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, acrylamide, methacrylamide, styrene, ≪ / RTI >
The alkali developable binder polymer of the present invention is a polymer having a number average molecular weight of 30,000 to 150,000 and a glass transition temperature of 20 to 150 ° C in consideration of the coating property, followability, and mechanical strength of the resist itself after formation of a circuit, As a compound, from 40 to 70% by weight in the photosensitive resin composition. When the content of the alkali developable binder polymer is within the above range, an effect of enhancing the fine line adhesion force after the circuit formation can be obtained.
[C] Photopolymerizable compound
The photopolymerizable compound of the present invention has resistance to a developer after UV exposure and enables pattern formation. The photopolymerizable compound of the present invention may comprise monomers having at least two ethylene groups at the terminals.
Examples of the monomer having at least two ethylene groups at the terminal thereof include ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, But are not limited to, propylene glycol dimethacrylate, polypropylene glycol dimethacrylate, butylene glycol dimethacrylate, neopentyl glycol dimethacrylate, 1,6-hexane glycol dimethacrylate, trimethyolpropane trimethacrylate, trimethyolpropane triacrylate, glycerin dimethacrylate (also referred to as " glycerin dimethacrylate), pentaerythritol dimethacrylate Pentaerythritol dimethacrylate, pentaerythritol trimethacrylate, dipentaerythritol pentamethacrylate, 2,2-bis (4-methacryloxy diethoxyphenyl) propane (2, 2-bis (4-methacryloxypolyethoxyphenyl) propane, 2,2-bis (4-methacryloxypolyethoxyphenyl) propane, (2-hydroxy-3-methacryloyloxypropyl methacrylate), ethylene glycol diglycidyl ether dimethacrylate, diethylene glycol diglycidyl ether dimethacrylate diethylene glycol diglycidyl ether dimethacrylate, phthalic acid diglycidyl ester dimethacrylate, glycerin polyglycidyl ether, l ether polymethacrylate) and a polyfunctional (meth) acrylate containing a urethane group.
The content of the photopolymerizable compound is preferably 10 to 50% by weight in the photosensitive resin composition. When the content of the photopolymerizable compound is within the above range, the effect of enhancing photosensitivity, resolution, adhesion and the like can be obtained.
[D] Other additives
The photosensitive resin composition of the present invention may further contain other additives as necessary. Examples of other additives include dibutyl phthalate, diheptyl phthalate, dioctyl phthalate, diallyl phthalate, Triethylene glycol diacetate in the glycol ester form, tetraethylene glycol diacetate; P-toluenesulfonamide in the acid amide form, benzenesulfonamide, n-butylbenzenesulfonamide; Triphenyl phosphate and the like can be used.
In the present invention, a leuco dye or a coloring material may be added to improve the handleability of the photosensitive resin composition.
Examples of the Luco dyes include tris (4-dimethylamino-2-methylphenyl) methane, tris (4-dimethylamino-2-methylphenyl) methane and fluororan dyes. Among them, when Luco Crystal Violet is used, the contrast is favorable. The content of the leuco dye is preferably 0.1 to 10% by weight in the photosensitive resin composition. From the viewpoint of the appearance of contrast, the content is preferably 0.1% by weight or more, and 10% by weight or less from the viewpoint of maintaining storage stability.
Examples of the coloring materials include toluenesulfonic acid monohydrate, fuchsin, phthalocyanine green, aramine base, paramagenta, crystal violet, methyl orange, nile blue 2B, Victoria blue, malachite green, diamond green, . When the coloring material is contained, the amount added is preferably 0.001 to 1% by weight in the photosensitive resin composition. When the content is 0.001% by weight or more, there is an effect of improving handling properties. When the content is 1% by weight or less, storage stability is maintained.
Other additives may further include heat polymerization inhibitors, dyes, discoloring agents, adhesion promoters, and the like.
In the present invention, the photosensitive resin composition having the above composition may be prepared from a photosensitive resin composition for a dry film photoresist. The photosensitive resin composition may be coated on a conventional base film such as polyethylene terephthalate by a conventional coating method to a thickness of 10 to 400 占 퐉 The photosensitive resin layer is coated and dried, and the dried photosensitive resin layer is laminated on the upper surface using a conventional protective film such as polyethylene to produce a dry film. The thus prepared dry film is subjected to a method of evaluating physical properties by exposure and development. It is preferable to use a laser direct exposure device including UV, visible light laser, etc. for the exposure.
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 to 5 and Comparative Example One]
The photosensitive resin composition for a dry film photoresist was evaluated by combining and coating according to the composition shown in Table 1 below. First, photopolymerization initiators were dissolved in methyl ethyl ketone (MEK) and methanol (MeOH) as solvents. Then, a photopolymerizable monomer and an alkali developable binder polymer were added and mixed for about 1 hour using a mechanical stirrer to obtain a photosensitive resin composition Respectively. The photosensitive resin composition thus obtained was coated on a 30 mu m PET film using a coating bar. The coated photosensitive resin composition layer was dried using a hot air oven at a drying temperature of 80 ° C. and a drying time of 5 minutes. The thickness of the photosensitive resin composition layer after drying was 30 μm. The dried film was laminated on the photosensitive resin layer using a protective film (PE).
The reactivity of the dry film was determined by laminating the dry film on a CCL using a lamination equipment (Hakuto Mach610i) at 110 ° C, a lamination roll pressure of 4 kgf / cm 2 and a speed of 2.0 m / min, placing the Stuffer Step Tablet on the surface of the dry film , And INPREX IP-3600H. The exposed dry film was developed in a 1 wt% aqueous solution of Na 2 CO 3 at 30 ° C and a spray pressure of 1.5 kgf / cm 2.
The circuit properties of the dry film were evaluated using a KOLON Test Artwork at a given sensitivity, and the results are shown in Table 2 below.
(ADEKA)
(Solid content 50%)
(1) BCIM: 2,2'-bis (2-chlorophenyl) -4,4'-5,5'-tetraphenylbisimidazole
(2) BPE-500: (2,2-bis [4- (methacryloxypolyethoxy) phenyl] propane
(3) M281: polyethylene glycol dimethacrylate
(4) A-TMPT-3EO: trimethylolpropane triacrylate
(5) 75ANEP-600: Nonylphenoxy poly (ethyleneglycolpropyleneglycol) monoacrylate
(6) KOLON BP-1: Methacrylic acid: Acrylic acid: Methylmethacrylate = 10: 10: 80 ratio of linear polymer
Using the dry film photoresist prepared in the above Examples and Comparative Examples, the exposure amount, photosensitivity, fine line adhesion, resolution and peelability of the copper plate were measured as follows, and the results are shown in Table 2 below.
(1) Measurement of exposure dose
And exposed using an exposure apparatus Paragon Ultra 80.
(2) Photosensitivity measurement
The sensitivity used as a measure of reactivity was measured on a resist basis using a 21-step tablet from Stouffer Graphic Arts Equipment Co.
(3) Measurement of adhesion of fine wire
After the PE film of the photosensitive dry film resist prepared in Examples 1 to 5 and Comparative Example 1 was removed, lamination was performed on a copper plate using a hot press roller. After exposing and developing the resist using a phototool having a wiring pattern of 10 to 150 mu m divided into 5 mu m units, the adhesion of the resist was measured.
The wiring pattern of adhesion is Line / Space = x: 400 (unit: 占 퐉), and the minimum value of the straight line excluding the meandering line among the independent fine lines is read in Table 2.
(4) Resolution measurement
Line / space = 10: 10-150: 150 (unit: 占 퐉), and the resist resolution was measured. The resolution of the resist pattern formed by the development after exposure is shown in Table 2 by reading the minimum value of the pattern in which the unexposed portions are cleanly removed.
(5) Measurement of peelability
The PE film of the prepared photosensitive dry film resist was removed, laminated on a copper plate using a heat press roller, exposed to light, and developed to produce a photocured film having a size of 50 mm x 50 mm. And peeling was performed using a 3% aqueous solution of sodium hydroxide (at a temperature of 50 ° C). The evaluation of the peelability was determined as the peeling time at which the photocured film fell off the copper plate. After the peeling, the size of the peeling specimen was measured and is shown in Table 2 as the following notation.
S: Small (Lower than 0.5cm)
M: Medium (0.5 to 2 cm)
L: Large (2 to 5 cm)
As shown in Table 2, the photosensitivity of Examples 1 to 5 was improved at the same exposure amount compared to Comparative Example 1, and it was confirmed that the thin line adhesion, resolution, and workability of Examples 1 to 5 exhibited equivalent or superior physical properties to those of Comparative Example 1 I could.
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 (4)
[Chemical Formula 1]
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| Application Number | Priority Date | Filing Date | Title |
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| KR1020120155793A KR20140087164A (en) | 2012-12-28 | 2012-12-28 | Photosensitive Resin Composition for Dry Film Photoresist |
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| KR1020120155793A KR20140087164A (en) | 2012-12-28 | 2012-12-28 | Photosensitive Resin Composition for Dry Film Photoresist |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160080408A (en) * | 2014-12-29 | 2016-07-08 | 코오롱인더스트리 주식회사 | Photosensitive resin composition for Dry Film Photoresist |
| JP2020190735A (en) * | 2020-07-14 | 2020-11-26 | 旭化成株式会社 | Photosensitive resin composition, photosensitive resin laminate, method for forming resist pattern and method for producing conductor pattern |
-
2012
- 2012-12-28 KR KR1020120155793A patent/KR20140087164A/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160080408A (en) * | 2014-12-29 | 2016-07-08 | 코오롱인더스트리 주식회사 | Photosensitive resin composition for Dry Film Photoresist |
| JP2020190735A (en) * | 2020-07-14 | 2020-11-26 | 旭化成株式会社 | Photosensitive resin composition, photosensitive resin laminate, method for forming resist pattern and method for producing conductor pattern |
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