CN109828436A - A kind of high attachment etch resistant photosensitive resin composition - Google Patents
A kind of high attachment etch resistant photosensitive resin composition Download PDFInfo
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- CN109828436A CN109828436A CN201910267870.8A CN201910267870A CN109828436A CN 109828436 A CN109828436 A CN 109828436A CN 201910267870 A CN201910267870 A CN 201910267870A CN 109828436 A CN109828436 A CN 109828436A
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Abstract
The invention discloses a kind of high attachment etch resistant photosensitive resin compositions, the photosensitive resin composition is mainly by 45-70wt% weight average molecular weight 50,000-150,000 alkali-soluble copolymer resin, the olefinic optical polymerism unsaturated monomer of 15-45wt%, the Photoepolymerizationinitiater initiater of 1-10wt% and 0.5-5wt% additive composition, wherein, the alkali-soluble fluoropolymer resin is formed by cyclenes class acid anhydrides, (methyl) acrylic acid and acrylic ester compound free radical polymerization containing double hexatomic ring rigid structures.Photosensitive resin composition comprising above-mentioned alkali-soluble fluoropolymer resin has high adhesion property, good resolution and elching resistant energy, effectively reduces the generation of breaking phenomena in etch process, greatly improves yield and efficiency in PCB production process.
Description
Technical field
The present invention relates to a kind of resin combination more particularly to a kind of high attachment etch resistant photosensitive resin compositions.
Background technique
Dry film photoresist (Dry Film Photoresist, DFR) is widely used as printed circuit board, lead frame, half
The critical material of pattern transfer in conductor encapsulating material, often through photosensitive resin composition is laminated on supporter, then
A protective layer is covered on the photosensitive resin composition as needed to prepare.And photosensitive resin composition therein is
DFR core, usually by containing the alkali soluble resin polymer for having carboxyl, at least containing a terminal ethylene type unsaturated group
Olefinic photo polymerization monomer, the poly- initiator of light and other additives mixing composition.
When making printed wiring board using DFR, process is generally pad pasting, lamination, exposure, development, thus on substrate
Form corrosion-resisting pattern.After corrosion-resisting pattern is formed, the technique for forming circuit is broadly divided into two kinds, cap bore method and plating.Cap bore
Method be to not by resist pattern cover copper-clad laminate on naked copper surface be etched, then with than developer solution alkalinity
It is stronger to move back film liquid removal resist pattern, the method for leaving line pattern identical with resist pattern.Plating is by upper
It states and is not electroplated by the naked copper surface on the copper-clad laminate of corrosion-resisting pattern covering, then removed identically as cap bore method anti-
Corrosion figure case is further etched to moving back exposed copper face after film, and generally by acid solutions such as copper chloride, iron chloride when etching
At.
From production technology angle, in process against corrosion and plating, the adhesion property and etch resistant of dry film photoresist
Performance is particularly important.In cap bore method, in order not to make etching solution along solidify line edges against corrosion invade profit to etchant resist and copper face it
Between, there must be excellent close knot between resist and copper.Once due to resist in conjunction with copper face it is not close with it is secured, erosion
It carves liquid infiltration to enter, route against corrosion floats, then will lead to and need to form the copper of circuit part and be etched, form up-narrow and down-wide electricity
Road figure even causes breaking problem.It is consistent with cap bore method, in plating in order not to make electroplate liquid penetrate into resist and copper face it
Between, plating phenomenon is caused in electroplating line edge formation burr shape, the unexpected solder figure of convex.
In order to which with the line map of higher yield manufacture thin space, wiring board manufacturer then proposes dry film photoresist performance
Higher basic requirement, high-resolution, high attachment.From going to prepare line map with higher production efficiency, then require dry
Film resist has that developing powder is fast, characteristics such as short of moving back the film time.In order to improve the adhesive force of dry film photoresist, amino is such as used
The monomer of formic acid ester structure finds that elching resistant and resistance to plating properties, coloring are improved (tekiaki 63- to a certain extent
No. 184744 bulletins), but resolution is inadequate.
Therefore, it currently needs one kind to have high attachment etch resistant photosensitive resin composition, is prepared into photosensitive dry film resist
Analysis feature is excellent afterwards, and adhesion is good and etch resistant, to promote CPB board production efficiency and yields.
Summary of the invention
The purpose of the invention is to make up the deficiencies in the prior art, a kind of high attachment etch resistant lightsensitive resin composition is provided
Object, the photosensitive resin composition is coated to be prepared into photosensitive dry film resist dry film route pair after pad pasting, exposure, developing process
There is excellent adhesion strength and good resolution using metal plate in PCB.
The purpose of the present invention is what is be achieved through the following technical solutions: a kind of high attachment etch resistant photosensitive resin composition,
The photosensitive resin composition mainly by 45-70wt% weight average molecular weight 50,000-150,000 alkali-soluble copolymer resin
Rouge, the olefinic optical polymerism unsaturated monomer of 15-45wt%, 1-10wt% Photoepolymerizationinitiater initiater and 0.5-5wt% additive
Composition, wherein the solvable soluble copolymer resin of alkali is as shown in general structure (I) containing double hexatomic ring rigid structures
(methyl) acrylic acid shown in cyclenes class acid anhydrides, general structure (II), (methyl) acrylate shown in general structure (III) are certainly
It is polymerized by base.
Wherein, R1、R2Separately it is selected from hydrogen atom, methyl, ethyl, propyl, isopropyl.
Wherein, R3For hydrogen atom or methyl.
Wherein, R4For hydrogen atom or methyl, R5Selected from C1-C18Alkyl, C2-C6Alcoxyl
Base.
Further, the alkali-soluble copolymer resin has following general formula (I)x(Ⅱ)y(Ⅲ)z, wherein x, y, z is divided
It Biao Shi I, II, III specific gravity in alkali soluble resin, wherein x 5-20wt%, y 20-35wt%, z 45-
60wt%.
Further, the alkali-soluble copolymer resin acid value exists in 110-200mg KOH/g resin, weight average molecular weight
50,000-150,000, molecular weight distribution is in 1.3-2.5.
Further, the olefinic optical polymerism unsaturated monomer is by (methyl) acrylate containing structure of bisphenol A；It is poly-
Ethylene glycol system two (methyl) acrylate；Polypropylene glycol system two (methyl) acrylate；Two (first of polyoxyethylene oxypropylene system
Base) acrylate；(methyl) alkyl acrylate；Trimethylolpropane tris (methyl) acrylate；Oxyalkylated trihydroxy methyl
Propane triacrylate；Pentaerythrite three (methyl) acrylate；Alkoxylate pentaerythrite three (methyl) acrylate；Season penta
Tetrol four (methyl) acrylate；Alkoxylate pentaerythrite four (methyl) acrylate；Dipentaerythritol four (methyl) propylene
Acid esters；Alkoxylate dipentaerythritol four (methyl) acrylate；Nonyl phenol (methyl) acrylate；Alkoxylated nonyl phenol
(methyl) acrylate；Phenoxyethyl (methyl) acrylate；The one of alkoxylated phenoxy ethyl (methyl) acrylate
Kind is a variety of by any proportion mixing composition.
Further, (methyl) acrylic ester compound containing structure of bisphenol A is selected from bisphenol-A two (methyl) third
Olefin(e) acid ester, ethoxyquin (the third oxidation) bisphenol a dimethacrylate, bisphenol A diglycidyl ether dimethylacrylate, preferably
For bisphenol-A two (methyl) acrylate.
Further, described (methyl) acrylate is preferably methyl methacrylate, ethyl acrylate, acrylic acid fourth
Ester.
Further, the Photoepolymerizationinitiater initiater is hexa-aryl bi-imidazole derivative.
Further, the Photoepolymerizationinitiater initiater can be by 2,2 ', 4- tri- (2- chlorphenyl) -5- (3,4- dimethoxy benzenes
Base) -4 ', 5 '-diphenyl -1,1 '-diimidazole, 2- (Chloro-O-Phenyl) -4,5- diphenyl-imidazole dimer, 2- (Chloro-O-Phenyl) -
One of 4,5- bis- (methoxyphenyl) imidazole dimer, 2- (o-fluorophenyl) -4,5- diphenyl-imidazole dimer are a variety of
It is formed according to any proportion mixing, further preferably 2,2 ', 4- tri- (2- chlorphenyl) -5- (3,4- Dimethoxyphenyl) -4 ',
5 '-diphenyl -1,1 '-diimidazole.
Further, additive is by one of light colour coupler, quality heat stabilizer, plasticizer, antioxidant, deodorant
Or it is a variety of by any proportion mixing composition.
The beneficial effects are mainly reflected as follows: the present invention is utilized introduces double six in alkali soluble resin polymerized monomer
The acid anhydrides of member ring rigid structure can effectively enhance the binding ability and etch-resistance energy to substrate copper sheet, to reduce figure electrician
Plating, the short circuit, breaking phenomena occurred in skill.
Specific embodiment
Alkali soluble resin is one of core component of photosensitive resin composition, and functional monomer, which is pointedly added, to be shown
Land the comprehensive performances such as the adhesion strength for promoting photosensitive resin composition, developing rate, storage stability, etch-resistance.
The invention discloses a kind of high attachment etch resistant photosensitive resin compositions, and the present invention is described more particularly below.
Of the invention is also characterized by by that will introduce functional monomer simultaneously from alkali soluble resin main polymer chain
Be applied in photosensitive resin composition, provide it is a kind of for PCB using metal plate have excellent adhesion strength, and efficiently
Developing rate and development after the characteristics such as resolution is good high attachment etch resistant photosensitive resin composition.
Presently preferred embodiments of the present invention and comparative example are illustrated below.But following embodiments are in the present invention
Preferable embodiment be not intended to limit the present invention.
1. acid anhydrides TM of the synthesis containing double six annulus rigid structures
Maleic anhydride (MA) is added in the four-hole boiling flask that thermometer, agitating device, dropping funel, condenser pipe are housed, stirs
It mixes and is warming up to melting, the activated silica gel relative to terpinene quality 6% is added as catalyst, is warming up to 140 DEG C of dropwise addition pine tars
Alkene, about holding 2h are added dropwise, and terpinene and maleic anhydride amount ratio are 1.8:1, and it is anti-to then raise temperature to 150 DEG C of holding constant temperature
2.5h is answered, sampling examines redfree with n,N-Dimethylaniline, i.e. maleic anhydride has reacted, and room temperature is down in water-bath, and toluene is added
Dilute reaction solution filters after removing catalyst, is evaporated under reduced pressure out toluene and unreacted terpinene, collect 190~200 DEG C (1.1~
1.3k Pa) under fraction be maleic anhydride (TM) that addition product contains double six annulus rigid structures.
2. synthesizing following alkali-soluble copolymer resin Z.
It is prepared using free radical solution polymerization, comprising the following steps:
Alkali-soluble polymer monomers are uniformly mixed according to certain quality proportioning (total 100g), initiator is added
AIBN, is added 95g butanone and 15g ethyl alcohol, stirring and dissolving, by peristaltic pump to three with nitrogen protection, condensation reflux unit
The mixed solution of about 35% mass fraction is added in neck flask, oil bath heating is heated to 78 DEG C, is slowly added dropwise after being stirred to react 1h
Remaining mixed solution, adds in 3h.After continuing insulation reaction 4h, 90 DEG C are warming up to, adds cause dissolved with 0.2g in two times
The 20g butanone solution of agent, two minor ticks are 1h, rear insulated and stirred 2h are added dropwise, reaction was completed.Obtain alkali-soluble copolymer
Resin, GPC survey its weight average molecular weight and contain with molecular weight distribution and admittedly.
3. preparing Photosensitve resin composition
Photosensitive resin composition of the present invention is unsaturated single in addition to above-mentioned alkali-soluble copolymer resin, olefinic optical polymerism
Outside body, Photoepolymerizationinitiater initiater, additive is also needed, the additive is by light colour coupler, quality heat stabilizer, plasticizer, anti-oxidant
One of agent, deodorant are a variety of by any proportion mixing composition.The smooth colour coupler can use diamond green GH, procrypsis knot
Crystalviolet, trisbromomethyl phenyl sulfone, methyl orange, Viride Nitens 1, Viride Nitens 2, Viride Nitens 3, Viride Nitens 4, Viride Nitens 5, phthalocyanine blue, sieve
Red bright B's is one or more；Quality heat stabilizer can adopt methoxyl group phenol, hydroquinone, alkyl or aryl replace to benzene two
Phenol and benzoquinones, t-butyl catechol, pyrogallol, resin copper, β-phenol acid, 2,4- d-tert-butyl-p-cresol, 2,2- first
Base-bis- (4- ethyl -6- t-butyl phenols), to toluene benzoquinones, tetrahydro for 1,4-benzoquinone, aryl phosphites it is one or more；
Plasticizer can use benzotriazole, phthalic acid two (2- ethyl hexyl) ester, dibutyl phthalate, three fourth of citric acid
Ester, tributyl 2-acetylcitrate it is one or more；Antioxidant can select propionic acid octadecyl, 2,6 di-t-butyls to first
Phenol, dilauryl thiodipropionate, trisnonyl phenyl phosphite it is one or more；Deodorant can select the poly- certain herbaceous plants with big flowers alkene of hydrogenation,
Eugenol, polyoxyethylene laural (dodecane) base ether, Aerosol OT it is one or more, but be not limited to
This.
A series of alkali soluble resin Z-1~Z-5 are synthesized according to the formula of following table 1
Table 1: alkali soluble resin Z-1~Z-5 component table
According to the formula of following table 2, each component is mixed according to the proportion, a certain amount of butanone and ethyl alcohol is added, sufficiently
Stirring is configured to the solid photosensitive resin composition containing for 40% to being completely dissolved.
Table 2: photosensitive resin composition component list
4. preparing photosensitive dry film resist, select suitable bar and coating speed will be prepared by table 2 using coating machine
Photosensitive resin composition solution coating is in 15 μm of PET film, being placed in baking oven dry 8min.Hot rubber is used after cooling
Pressure roller, certain pressure at a temperature of 18 μ m thick of thermal-adhering PE film, to obtain photosensitive resin composition thickness and be
38 μm of dry film photoresist.
Testing example and comparative example:
By embodiment 1-10 and comparative example 1-3 photosensitive dry film resist, evaluated using the ultraviolet curable resin thickness of 38 μ m-thicks
Adhesion strength and resolution ratio.
[pad pasting]: copper-clad plate is processed by shot blasting its copper surface through sander, and washing is dried, and obtains bright fresh
Copper surface.It is 110 DEG C, conveying speed 1.5m/min that laminator roller temperature, which is arranged, thermal-adhering under normal pressure.
[exposure]: it is exposed using the holy science and technology M-552 type exposure machine of will, is carried out using 21 lattice exposure guide rule of stouffer
Light sensitivity test.
[development]: the selected film line width/line-spacing that develops progressively increases to 100um from 10um；Developer solution is 1wt% carbon
Acid sodium aqueous solution, development temperature are 30 DEG C, developer pressure 1.8bar, and developing powder is 1.5 ms/min, developing machine model
Remote Soviet Union science and technology XY-430.The resist layer of unexposed portion is completely dissolved the minimum time of needs as minimum developing time.
[resolution ratio evaluation]: the mask for the wiring pattern that the width with exposed portion and unexposed portion is 1:1 is utilized
It is exposed, shows movie queen with the 1.5 of minimum developing time, the minimum mask width for solidifying resist line will have been normally formed and made
For the value of resolution ratio.
[adhesion strength evaluation]: photosensitive dry film resist is laminated on copper sheet by hot pressing pad pasting, using with exposed portion
The mask for the wiring pattern that width with unexposed portion is n:400 is exposed, with 1.5 times of developments of minimum developing time
Afterwards, the minimum mask width for solidifying resist line will have been normally formed as the value of adhesive force.
[adhesion strength is evaluated after etching]: the copper sheet after development is etched technique, etching solution is copper chloride, etching speed
For 2.2m/min, etch temperature is 48 DEG C, is sprayed as 1.5bar, specific gravity 1.3g/mL, acidity 2mol/L, copper ion 140g/L, erosion
Quarter machine model DF-JYD300；The minimum mask width of line against corrosion will be solidified as the value of adhesive force after etching.
[evaluation result]
Embodiment and the evaluation result of comparative example such as table 3 show.
Table 3: evaluation result table
It can significantly be found by embodiment 1-10 and comparative example 1-3, relative to being not added with double hexatomic ring rigid structures
Cyclenes class anhydride structural unit Alkali-soluble acrylic tree, i.e. pure acrylate resin prepared dry film (comparative example 1-3), is implemented
Example 1-10 dry film its adhesive force decline degree after undergoing etch process is lower.8 embodiments of embodiment 6,7 and remaining are etched
Adhesive force declines 5 μm and 0-3 μm respectively afterwards, and comparing result is it is found that the cyclenes class acid anhydrides TM with double six annulus rigid structures contains
Amount increases, and the elching resistant of dry film is constantly promoted.Comparative example 1-4 is it is found that resin content can seriously affect dry film
Differentiate and attachment differentiate when resin content is 62% or so and can reach optimum value with attachment, respectively 30 μm with 35 μm.
Comparative example 5,9,10 is led when molecular weight is excessively high it is found that when too low alkali soluble resin molecular weight causes adhesion property to decline
Cause resolution performance bad.In conclusion the present invention can provide a kind of high attachment etch resistant photosensitive resin composition, the sense of preparation
Light dry film photoresist can further promote PCB production efficiency and yields in actual production and application process.
Claims (9)
1. a kind of high attachment etch resistant photosensitive resin composition, which is characterized in that the photosensitive resin composition is mainly by 45-
70wt% weight average molecular weight is in the alkali-soluble copolymer resin of 50,000-150,000, the olefinic optical polymerism of 15-45wt%
Unsaturated monomer, the Photoepolymerizationinitiater initiater of 1-10wt% and 0.5-5wt% additive composition, wherein the solvable dissolubility of alkali is total
Copolymer resin is as shown in general structure (I) containing pair the cyclenes class acid anhydrides of hexatomic ring rigid structures, general structure (II) institute
(methyl) free radical acrylate shown in (methyl) acrylic acid for showing, general structure (III) is polymerized.
Wherein, R1、R2Separately it is selected from hydrogen atom, methyl, ethyl, propyl, isopropyl.
Wherein, R3For hydrogen atom or methyl.
Wherein, R4For hydrogen atom or methyl, R5Selected from C1-C18Alkyl, C2-C6Alkoxy.
2. high attachment etch resistant photosensitive resin composition according to claim 1, which is characterized in that the alkali-soluble is total
Copolymer resin has following general formula (I)x(Ⅱ)y(Ⅲ)z, wherein x, y, z respectively indicates I, II, III in alkali soluble resin
Specific gravity, wherein x 5-20wt%, y 20-35wt%, z 45-60wt%.
3. high attachment etch resistant photosensitive resin composition according to claim 1, which is characterized in that the alkali-soluble is total
Copolymer resin acid value is in 110-200mg KOH/g resin, and weight average molecular weight is 50,000-150,000, and molecular weight distribution is in 1.3-
2.5。
4. olefinic optical polymerism unsaturated monomer according to claim 1, which is characterized in that the olefinic optical polymerism is not
Monomer is saturated by (methyl) acrylate containing structure of bisphenol A；Polyethylene glycol system two (methyl) acrylate；Polypropylene glycol system
Two (methyl) acrylate；Polyoxyethylene oxypropylene system two (methyl) acrylate；(methyl) alkyl acrylate；Three hydroxyls
Methylpropane three (methyl) acrylate；Triacrylic ester of alkoxylating trimethylolpropane；Pentaerythrite three (methyl) propylene
Acid esters；Alkoxylate pentaerythrite three (methyl) acrylate；Pentaerythrite four (methyl) acrylate；Alkoxylate Ji Wusi
Alcohol four (methyl) acrylate；Dipentaerythritol four (methyl) acrylate；Alkoxylate dipentaerythritol four (methyl) propylene
Acid esters；Nonyl phenol (methyl) acrylate；Alkoxylated nonyl phenol (methyl) acrylate；Phenoxyethyl (methyl) acrylic acid
Ester；The one or more of alkoxylated phenoxy ethyl (methyl) acrylate are formed by the mixing of any proportion.
5. olefinic optical polymerism unsaturated monomer according to claim 4, which is characterized in that described to contain structure of bisphenol A
(methyl) acrylic ester compound be selected from bisphenol-A two (methyl) acrylate, ethoxyquin (third oxidation) bisphenol-A dimethyl propylene
Olefin(e) acid ester, bisphenol A diglycidyl ether dimethylacrylate, preferably bisphenol-A two (methyl) acrylate.
6. high attachment etch resistant photosensitive resin composition according to claim 1, which is characterized in that (methyl) propylene
Acid esters is preferably methyl methacrylate, ethyl acrylate, butyl acrylate.
7. high attachment etch resistant photosensitive resin composition according to claim 1, which is characterized in that the photopolymerization causes
Agent is hexa-aryl bi-imidazole derivative.
8. high attachment etch resistant photosensitive resin composition according to claim 7, which is characterized in that the photopolymerization causes
Agent can be by 2,2 ', 4- tri- (2- chlorphenyl) -5- (3,4- Dimethoxyphenyl) -4 ', 5 '-diphenyl -1,1 '-diimidazole, 2-
(Chloro-O-Phenyl) -4,5- diphenyl-imidazole dimer, two (methoxyphenyl) imidazole dimer of 2- (Chloro-O-Phenyl) -4,5-, 2-
One of (o-fluorophenyl) -4,5- diphenyl-imidazole dimer is a variety of according to any proportion mixing composition, further preferably
It is 2,2 ', 4- tri- (2- chlorphenyl) -5- (3,4- Dimethoxyphenyl) -4 ', 5 '-diphenyl -1,1 '-diimidazole.
9. high attachment etch resistant photosensitive resin composition according to claim 1, which is characterized in that additive is by light quality
One of agent, quality heat stabilizer, plasticizer, antioxidant, deodorant are a variety of by any proportion mixing composition.
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| CN105938297A (en) * | 2015-03-04 | 2016-09-14 | 太阳油墨制造株式会社 | Etching resisting composition and dry film |
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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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