CN104407500A - Photosensitive resin composition with good side morphology - Google Patents
Photosensitive resin composition with good side morphology Download PDFInfo
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Abstract
The invention discloses a photosensitive resin composition, a dry film image of which is formed by exposure and development, has good side morphology and a higher resolution ratio. The resin capable of performing photopolymerization as a main component has the following structural general formula: (A)u(B)v(C)w(D)x(E)y(F)z, wherein A is methacrylic acid, B is acrylic acid, C is methyl methacrylate, D is dodecyl acrylate, E is (methyl) acrylate with a carbon chain number of 3-8, and F is phenoxyl ethyl acrylate. The photosensitive resin composition provided by the invention can be used as an etching resist material for the fields of printed circuit boards, lead frames, semiconductor encapsulation, precision machining of metal, and has the characteristics of good photosensitivity, high resolution ratio and good side morphology.
Description
Technical field
The present invention relates to a kind of photosensitive resin composition with good side pattern, the dry film image formed after exposure, development has good side pattern and higher resolution.
Background technology
Since ultraviolet curable resin polymkeric substance comes out, ultraviolet curable resin polymkeric substance has become the important materials of hyundai electronics field, particularly art of printed circuit boards.
In recent years, along with the Highgrade integration of electronic equipment, the demand of the high integrated circuit with narrow distribution and thin space figure is constantly increased.In order to prepare thin space figure with higher qualification rate, requiring that dry film is avoided producing surface imperfection, as figures such as zigzags, also just meaning that dry film must have good side pattern and higher resolution.
Jap.P. JP07333846 proposes a kind of method improving side pattern, is regulated, but there is limitation by the side pattern of alkali soluble resins to ultraviolet curable resin polymkeric substance of two kinds of different molecular weights and composition.These two kinds of alkali soluble resins performances can not be completely compatible, and the resolution of ultraviolet curable resin polymkeric substance will be made to decline.European patent EP 0909990 improves the side pattern of ultraviolet curable resin polymkeric substance by changing the ratio of (methyl) acrylic compounds alkali soluble resins, component and preparation method, can obtain the image that side pattern is good.But regrettably, this patent is not discussed to many major issues such as resolution, exposure energy.
Summary of the invention
The object of the invention is for the deficiencies in the prior art, a kind of photosensitive resin composition with good side pattern is provided.
The object of the invention is to be achieved through the following technical solutions: a kind of photosensitive resin composition with good side pattern, comprises: the alkali soluble resins of 50-70% massfraction, the monomer of the carried out optical free radical polyreaction of 25-45% massfraction, the light trigger of 0.1-10% massfraction; Described alkali-soluble resin has following general formula: (A)
u(B)
v(C)
w(D)
x(E)
y(F)
z; Wherein, A is methacrylic acid, and B is acrylic acid, and C is methyl methacrylate, and D is lauryl acrylate, (methyl) acrylate of E to be carbochain number be 3-8, and F is phenoxyethyl acrylate; U, v, w, x, y, z represent A, B, C, D, E, F mass percent in alkali soluble resins respectively; Wherein, u is 10-25%; V is 5-15%; W is 30-50%; X is 5-15%; Y is 5-18%; Z is 5-15%.
Further, described alkali soluble resins weight-average molecular weight is 30000-120000.
Further, described E is n-BMA or n-butyl acrylate.
Further, the gross mass mark of described A and B in alkali soluble resins is less than 27%.
Further, the described monomer carrying out optical free radical polyreaction at least contains di(2-ethylhexyl)phosphate (hydroxy ethyl) ester.
Further, the massfraction of described light trigger is 0.5-5%.
Further, described light trigger to be mixed according to any proportioning by one or more in benzoin ether, benzophenone and derivant thereof, thioxanthone system compounds, anthraquinone and derivant thereof, thioxanthones series compound, hexa-aryl bi-imidazole series compound and forms.
Further, described light trigger is at least containing 2,4,5-triarylimidazoles dimer or the dimeric derivant of 2,4,5-triarylimidazoles.
Further, described photosensitive resin composition also comprises the adjuvant of 0 ~ 1 weight portion, and described adjuvant is combined according to any proportioning by one or more in organic dyestuff, levelling agent and plastifier.
The invention has the beneficial effects as follows: Photosensitve resin composition provided by the invention, in the fields such as its Precision Machining at printed circuit board (PCB), lead frame, semiconductor packages, metal, as resist material against corrosion, there are the characteristics such as good photosensitivity, resolution and side pattern, be conducive to the qualification rate improving PCB batch production, enhance productivity, reduce production cost.
Embodiment
A kind of photosensitive resin composition, comprises: the alkali soluble resins of 50-70% massfraction, the monomer of the carried out optical free radical polyreaction of 25-45% massfraction, the light trigger of 0.1-10% massfraction; Described alkali soluble resins has following general formula: (A)
u(B)
v(C)
w(D)
x(E)
y(F)
z;
Wherein, A is methacrylic acid, and B is acrylic acid, and C is methyl methacrylate, and D is lauryl acrylate, (methyl) acrylate of E to be carbochain number be 3-8, and F is phenoxyethyl acrylate; U, V, W, X, Y, Z represent A, B, C, D, E, F mass percent in alkali soluble resins respectively; Wherein, U is 10-25%; V is 5-15%; W is 30-50%; X is 5-15%; Y is 5-18%; Z is 5-15%.
The alkali soluble resins weight-average molecular weight used in the present invention is 30000-120000, from improving the angle of developability, and preferably 120000 and following; Cover hole ability from raising, suppress Fusion Edges angle, preferably 30000 and more than.More preferably 60000-90000.
In alkali soluble resins, (methyl) acrylate of E to be carbochain number be 3-8, is preferably (methyl) acrylate that carbochain number is 4-6, is more preferably n-BMA or n-butyl acrylate, most preferably is n-BMA.
In order to the developing performance of the reliability and photosensitive resin composition that improve pad pasting, the gross mass mark of described A and B in alkali soluble resins is less than 27%.
The described monomer carrying out Raolical polymerizable, at least can the ethene unsaturated functional group of polymerization reaction take place containing one in its molecule, and this monomer can carry out being polymerized or cross-linking reaction with alkali soluble resins after absorption luminous energy.Relative to the ratio of whole optical polymerism resin combination, be preferably 25-45% mass ratio.Described monomer both can be mono-functional compounds can be also polyfunctional compound, and wherein mono-functional compounds is lauryl acrylate, isodecyl acrylate, acrylic acid tetrahydrofuran methyl esters, the luxuriant ester of the third olefin(e) acid two Evil etc.; Difunctional is polyethyleneglycol diacrylate, polypropylene glycol dimethacrylate, the acid of Ethoxylated bisphenol A diacrylate fat, 1,6-hexanediyl ester etc.; Polyfunctional group can be trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, propoxylation trihydroxy methyl propane triacrylate, glycerol propoxylate triacrylate, pentaerythritol triacrylate, tetramethylol methane tetraacrylate, dipentaerythritol acrylate etc.From the angle improving adhesion, it is at least containing di(2-ethylhexyl)phosphate (hydroxy ethyl) ester.
In the present invention, the ratio of light trigger is 0.1-10% weight ratio, from realizing good sensitivity, resolution, cohesiveness, and more preferably 0.5-5% weight ratio.
Light trigger can be that one or more in benzoin ether, benzophenone and derivant thereof, thioxanthone system compounds, anthraquinone and derivant thereof, thioxanthones series compound, hexa-aryl bi-imidazole series compound are used in combination.Specifically comprise: the two methyl ether of benzoin, benzoin ethyl ether, benzoin propyl ether, benzoin phenyl ether, thioxanthones, CTX, CTX, ITX, ITX, benzophenone, 4, 4 '-bis-(dimethylamino) benzophenone (michaelis ketone), 4, 4 '-bis-(lignocaine) benzophenone, isopropyl thioxanthone, 2-chlorothiaxanthenone, 2, 4-diethyl thioxanthone, 2-EAQ, 2-tert-butyl group anthraquinone, N, N-mesitylenic acid ethyl ester, benzoic acid dimethylaminoethyl, N, N-dimethylethanolamine, 2, 2 '-bis-(2-chlorphenyl)-4, 4 ', 5, 5 '-tetraphenyl-1, 2 '-diimidazole, 2, 2 '-bis-(bromo-5-methoxybenzene of 2-)-4, 4 ', 5, 5 '-tetraphenyl diimidazole, 2, 2 '-bis-(2, 4-dichlorophenyl)-4, 4 ', 5, 5 '-tetraphenyl diimidazole etc.From high resolving power and high sensitivity angle, at least containing hexa-aryl bi-imidazole series compound in light trigger, particularly preferably 2,2 ', 4-tri-(2-chlorphenyl)-5-(3,4-Dimethoxyphenyl)-4 ', 5 '-diphenyl-1,1 '-diimidazole.
Conveniently produce and be convenient to observe, also can add other materials in photosensitive resin composition, as organic dyestuff, levelling agent and plastifier, this is known technology in industry, does not repeat at this.
Be known method as method photosensitive resin composition being coated in support film.In ultraviolet curable resin polymkeric substance, add one or more be arbitrarily prepared into optical polymerism resin mixture liquor than the organic solvents mixed, these organic solvents the composition of photosensitive resin layer can be dispersed or dissolved and not with these component chemically reactives.Re-use coating machine to carry out applying, through super-dry, thermal-adhering protective seam on support membrane.Thus formation photosensitive dry film.Organic solvent can be acetone, butanone, methyl alcohol, ethanol, ethyl acetate, glycol monoethyl ether, glycol methyl ether acetate etc.For the ease of producing and operation, other adjuvant also comprises tackifier, chromophoric dyestuffs, hot polymerization inhibitor, antioxidant, levelling agent etc. are penetrated in plastifier, pigment, illumination.Support membrane is PET film, and thickness is 10-30 um; Covered with protective film is PE film, and thickness is 10-30 um.
Below preferred embodiment of the present invention and comparative example are described.But following embodiment is better embodiment in the present invention and unrestricted the present invention.
First, following alkali soluble resins polymkeric substance is prepared.
Under inert gas shielding; 150 mL butanone are added in the 500 mL three-necked bottles being furnished with mechanical stirrer, reflux condensing tube; by methacrylic acid/acrylic acid/methyl methacrylate/acrylic acid lauryl/n-BMA/phenoxyethyl acrylate according to 15/10/47/10/8/10 weight ratio be configured in the solution of 300 g, join in three-necked bottle.Be warming up to 80
oc.
Separately 1 g azoisobutyronitrile is dissolved in the butanone of 10 mL, is added drop-wise in three-necked bottle.Mixed liquor is in 80
obe polymerized 4 hours under C.Then, again drip the 10 mL butanone solutions being dissolved with 0.8 g azoisobutyronitrile, add thermal agitation 8 hours.After liquid to be mixed is down to room temperature, obtain binder solution A-1.GPC record its weight-average molecular weight (
m w ) be 82000, solid content is 40.8%.
Alkali soluble resins A-2, A3, A4 can be carried out, Comparative Example I-1, I-2, I3, I4 according to the synthesis of similar synthetic method.
Alkali soluble resins A-2: methacrylic acid/acrylic acid/methyl methacrylate/acrylic acid lauryl/n-butyl acrylate/phenoxyethyl acrylate=13/10/47/12/5/13(weight ratio) (
m w =78000, solid content is 40.4%).
Alkali soluble resins A-3: methacrylic acid/acrylic acid/methyl methacrylate/acrylic acid lauryl/n-butyl acrylate/phenoxyethyl acrylate=10/7/50/15/5/13(weight ratio) (
m w =120000, solid content is 40.5%).
Alkali soluble resins A-4: methacrylic acid/acrylic acid/methyl methacrylate/acrylic acid lauryl/EHMA/phenoxyethyl acrylate=10/5/40/15/18/12(weight ratio) (
m w =31000, solid content is 40.2%).
Comparative example:
I-1: methacrylic acid/acrylic acid/methyl methacrylate/acrylic acid lauryl/ethyl acrylate/phenoxyethyl acrylate=15/10/47/10/8/10(weight ratio) (
m w =86000, solid content is 41.1%).
I-2: methacrylic acid/acrylic acid/methyl methacrylate/acrylic acid lauryl/β-dimethyl-aminoethylmethacrylate/phenoxyethyl acrylate=13/10/47/12/5/13(weight ratio) (
m w =81000, solid content is 40.7%).
I-3: methacrylic acid/acrylic acid/methyl methacrylate/acrylic acid lauryl/lauryl methacrylate/phenoxyethyl acrylate=10/7/50/15/5/13(weight ratio) (
m w =95000, solid content is 40.3%).
I4: methacrylic acid/acrylic acid/methyl methacrylate/acrylic acid lauryl/ethyl acrylate/phenoxyethyl acrylate=10/5/40/15/18/12(weight ratio) (
m w =38500, solid content is 40.0%).
Prepare followingly can carry out photopolymerisable monomer:
B-1: di(2-ethylhexyl)phosphate (hydroxy ethyl) ester (Japanese chemical drug PM-2)
B-2: ethoxylated trimethylolpropane triacrylate (Tianjin proud son of heaven chemical industry EO9-TMPTA)
B-3: ethoxylated bisphenol a diacrylate (Tianjin proud son of heaven chemical industry EO4-BPADA)
B-4: trimethylolpropane triacrylate (U.S. Sartomer SR351NS)
Prepare following Photoepolymerizationinitiater initiater:
C-1:2,2 ', 4-tri-(2-chlorphenyl)-5-(3,4-Dimethoxyphenyl)-4 ', 5 '-diphenyl-1,1 '-diimidazole (Changzhou electronic strong material)
C-2:4,4 '-bis-(diethylamino) benzophenone (Changzhou electronic strong material)
C-3:2,4,5-triarylimidazoles dimer (West Asia chemistry)
Adjuvant:
D-1 diamond green (Shanghai ladder is uncommon likes chemical industry)
D-2 trisbromomethyl phenyl sulfone (Shanghai ladder is uncommon likes chemical industry)
D-3 leuco crystal violet (Shanghai ladder is uncommon likes chemical industry)
D-4 5-carboxyl benzotriazole (Shanghai lark waffle learn a skill company limited)
D-5 p-dihydroxy-benzene (Shanghai lark waffle learn a skill company limited)
Prepared by Photosensitve resin composition:
Free radical polymerizable monomer, adjuvant, Photoepolymerizationinitiater initiater are joined in alkali soluble resins solution, after dissolving completely, at room temperature stirs 4 hours, go out decon with 200 order filtrators, obtain Photosensitve resin composition.
The preparation of photosensitive dry film:
By Photosensitve resin composition, use bar coater to be uniformly coated on to the film that thickness is 30 μm in 15 μm of PET film, dry, use rubber rollers thermal-adhering 18 μm of thickness PE films, thus obtain photosensitive dry film.Photosensitve resin composition composition is as shown in table 1.
Table 1
The all photosensitive resin compositions of note: * all carry out testing after drying in coating film forming, and organic solvent is removed.
Testing example and comparative example:
Side pattern after using 30 μm of thick photosensitive resin layers to evaluate resolution and dry film development.
Pad pasting: utilize Changzhou electronics CYL-M25 that often shines to carry out thermal-adhering under standard pressure, laminating speed is 1 m/min, and binding temperature is 105
oc.
Exposure: use the holy scientific and technological M-552 type exposure machine of will to expose, use stouffer 21 lattice exposure guide rule to carry out exposure energy mensuration, exposure lattice number is 6-8 lattice, and exposure energy is 30-45 mJ/cm
2.
Development: the selected film live width/line-spacing of development is increased to 100um gradually from 10 um; Developer solution is 1% aqueous sodium carbonate, and development temperature is 30
oc, developer pressure is 1.8 bar, and developing powder is 1.5 ms/min, and developing machine model is the scientific and technological XY-430 of Soviet Union far away.The resist layer of unexposed portion is dissolved completely the minimum time of needs as minimum development time.
By SEM, sample is observed, enlargement ratio 500 times.
[resolution evaluation]
After the PE film of the photosensitive dry film resist manufactured by removing, Heating roll is utilized to carry out stacked dry film on copper coin.At this, utilize the mask of the wiring pattern that the width with exposed portion and unexposed portion is 1:1 to expose, show movie queen with 1.5 of minimum development time, will normally define the value of minimum mask width as resolution of solidification resist line.
◎: resolution value is for being less than or equal to 20 μm;
Zero: resolution value, for being greater than 20 μm, is less than or equal to 30 μm
▽: resolution value, for being greater than 30 μm, is less than or equal to 40 μm of △: resolution value is greater than 40 μm
[evaluation of side pattern]
After the PE film of the photosensitive dry film resist manufactured by removing, Heating roll is utilized to carry out stacked dry film on copper coin.At this, utilize the mask of the wiring pattern that the width with exposed portion and unexposed portion is 1:1 to expose, show movie queen with 1.5 of minimum development time, the dry film image of acquisition.
Good side pattern, refers to that the image side pattern that photosensitive resin composition is being formed after overexposure, development has following characteristics: (a) side does not exist zigzag pattern, does not have the defects such as pit; (2) side is straight, and perpendicular to copper substrate, does not expand in developer solution; C development latitude that () is higher
▲ side is straight, perpendicular to copper substrate, without obviously expanding and defect.
◆ side is straight, perpendicular to copper substrate, there is slight expansion and defect.
▼ lateral section region existing defects, exists and obviously expands.
● side indentation
[evaluation result]
The evaluation result of embodiment and comparative example is shown in table 2.
Table 2
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | |
| Resolution is evaluated | ◎ | ◎ | ○ | ○ | ◎ | ○ | ▽ | ○ | ▽ | △ |
| Side pattern is evaluated | ▲ | ▲ | ▲ | ◆ | ◆ | ▲ | ◆ | ▼ | ● | ● |
As shown in Table 2, Photosensitve resin composition provided by the invention, in the fields such as its Precision Machining at printed circuit board (PCB), lead frame, semiconductor packages, metal, as resist material against corrosion, there are the characteristics such as good photosensitivity, resolution and side pattern, be conducive to the qualification rate improving PCB batch production, enhance productivity, reduce production cost.
Claims (9)
1. there is a photosensitive resin composition for good side pattern, it is characterized in that, comprise: the alkali soluble resins of 50-70 weight portion, the monomer of the carried out optical free radical polyreaction of 25-45 weight portion, the light trigger of 0.1-10 weight portion; Described alkali-soluble resin has following general formula: (A)
u(B)
v(C)
w(D)
x(E)
y(F)
z; Wherein, A is methacrylic acid, and B is acrylic acid, and C is methyl methacrylate, and D is lauryl acrylate, (methyl) acrylate of E to be carbochain number be 3-8, and F is phenoxyethyl acrylate; U, v, w, x, y, z represent A, B, C, D, E, F mass percent in alkali soluble resins respectively; Wherein, u is 10-25%; V is 5-15%; W is 30-50%; X is 5-15%; Y is 5-18%; Z is 5-15%.
2. photosensitive resin composition according to claim 1, is characterized in that, described alkali soluble resins weight-average molecular weight is 30000-120000.
3. photosensitive resin composition according to claim 1, is characterized in that, described E is n-BMA or n-butyl acrylate.
4. photosensitive resin composition according to claim 1, is characterized in that, the gross mass mark of described A and B in alkali soluble resins is less than 27%.
5. photosensitive resin composition according to claim 1, is characterized in that, the described monomer carrying out optical free radical polyreaction comprises di(2-ethylhexyl)phosphate (hydroxy ethyl) ester.
6. photosensitive resin composition according to claim 1, is characterized in that, the massfraction of described light trigger is 0.5-5%.
7. photosensitive resin composition according to claim 1, it is characterized in that, described light trigger to be mixed according to any proportioning by one or more in benzoin ether, benzophenone and derivant thereof, thioxanthone system compounds, anthraquinone and derivant thereof, thioxanthones series compound, hexa-aryl bi-imidazole series compound and forms.
8. photosensitive resin composition according to claim 7, is characterized in that, described light trigger is 2,4,5-triarylimidazoles dimer or the dimeric derivant of 2,4,5-triarylimidazoles.
9. photosensitive resin composition according to claim 1, it is characterized in that, described photosensitive resin composition also comprises the adjuvant of 0 ~ 1 weight portion, and described adjuvant is combined according to any proportioning by one or more in organic dyestuff, levelling agent and plastifier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410763055.8A CN104407500B (en) | 2014-12-12 | A kind of photosensitive resin composition with good side pattern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410763055.8A CN104407500B (en) | 2014-12-12 | A kind of photosensitive resin composition with good side pattern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104407500A true CN104407500A (en) | 2015-03-11 |
| CN104407500B CN104407500B (en) | 2018-02-09 |
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ID=
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105573056A (en) * | 2015-12-18 | 2016-05-11 | 杭州福斯特光伏材料股份有限公司 | Light-sensing dry film resist |
| CN106909026A (en) * | 2017-03-31 | 2017-06-30 | 苏州福斯特光伏材料有限公司 | A kind of anti-corrosion agent composition and resist layer laminate that can directly describe exposure image |
| WO2023210746A1 (en) * | 2022-04-28 | 2023-11-02 | 大阪有機化学工業株式会社 | Polymer, curable resin composition, stretchable insulating cured film obtained by curing said composition, insulating cured film for touch panel, touch panel, insulating cured film for flexible printed circuit board, and flexible printed circuit board |
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| EP0529643B1 (en) * | 1991-08-30 | 1995-10-18 | Hercules Incorporated | Aqueous-developable dry film photoresist |
| JPH07333846A (en) * | 1994-06-09 | 1995-12-22 | Hitachi Chem Co Ltd | Photosensitive resin composition and photosensitive film using the same |
| US6180323B1 (en) * | 1997-08-27 | 2001-01-30 | E. I. Du Pont De Nemours And Company | Photopolymerizable compositions having improved sidewall geometry and development latitude |
| CN1734351A (en) * | 2004-08-09 | 2006-02-15 | 东进世美肯株式会社 | Photosensitive resin composition for isolator |
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| US4876173A (en) * | 1985-01-23 | 1989-10-24 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition on polyethylene terephthalate film support |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105573056A (en) * | 2015-12-18 | 2016-05-11 | 杭州福斯特光伏材料股份有限公司 | Light-sensing dry film resist |
| CN105573056B (en) * | 2015-12-18 | 2019-08-20 | 杭州福斯特应用材料股份有限公司 | A kind of photosensitive dry film resist |
| CN106909026A (en) * | 2017-03-31 | 2017-06-30 | 苏州福斯特光伏材料有限公司 | A kind of anti-corrosion agent composition and resist layer laminate that can directly describe exposure image |
| CN106909026B (en) * | 2017-03-31 | 2019-11-22 | 苏州福斯特光伏材料有限公司 | A kind of anti-corrosion agent composition that can directly describe exposure image and resist layer laminate |
| WO2023210746A1 (en) * | 2022-04-28 | 2023-11-02 | 大阪有機化学工業株式会社 | Polymer, curable resin composition, stretchable insulating cured film obtained by curing said composition, insulating cured film for touch panel, touch panel, insulating cured film for flexible printed circuit board, and flexible printed circuit board |
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