CN103529649A - Negative fluorine-containing photoresist composition and application thereof in preparation of polymer optical waveguide device - Google Patents
Negative fluorine-containing photoresist composition and application thereof in preparation of polymer optical waveguide device Download PDFInfo
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Abstract
The invention provides a negative fluorine-containing photoresist composition and an application thereof in preparation of a polymer optical waveguide device, and belongs to the technical field of polymer optical waveguide. The negative fluorine-containing photoresist composition comprises an epoxy-terminated fluorine-containing polycarbonate, a photo-acid generating compound (a photoinitiator) and an organic solvent; according to the weight percentage, the content of the epoxy-terminated fluorine-containing polycarbonate is 38-66 wt%, the content of the photo-acid generating compound is 8% of that of the epoxy-terminated fluorine-containing polycarbonate, and the balance is the organic solvent. By changing the type of the photo-acid generating compound, an exposure wavelength of the photoresist composition can be adjusted, and at the same time, because most of hydrogen atoms are replaced by fluorine atoms in the epoxy-terminated fluorine-containing polycarbonate, absorption at a communication wave band is smaller. The photoresist composition can be exposed and imaged to prepare the polymer optical waveguide device in an ultraviolet wavelength range of 200 nm-400 nm.
Description
Technical field
The invention belongs to polymer optical wave guide technical field, be specifically related to a kind of negative fluorine-contained photoetching compositions that can be used for preparing polymer optical waveguide device, this kind of composition is comprised of epoxy-capped fluorine-containing polycarbonate, photic acid-producing agent and organic solvent.
Background technology
Photoresist (photo-induced etching agent) is a kind ofly by the light source such as the optical, electrical sub-bundle of ultraviolet (UV), excimer laser, X-ray, ion beam, to irradiate or radiation causes the membraneous material of the etch resistant that its solubleness changes.Photoresist constituent, conventionally by polymer substrate, photo-acid generator and solvent composition, is mainly used in manufacturing miniature electronic part in microplate typography, as manufactured computer chip and integrated circuit.Because photoresist material has photochemical sensitivity, so can utilize it to carry out photochemical reaction, form curing and crosslinked.First by the thin film coated of photoresist constituent in substrate, the substrate that baking process subsequently applies is to remove the solvent in photoresist constituent, by mask plate, photoresist coating is exposed under radiation source, there is photic chemical change in photoresist thereupon, finally develops and obtain corresponding pattern.
The type of photoetching compositions have a positivity effect with two kinds of negative effects.When positive photoresist is subject to illumination, there is decomposition reaction, after development, obtain positive figure, and cross-linking reaction occurs when negative photoresist is subject to illumination, after development, obtain negative patterning, can select according to different needs.
At present, in ultraviolet thick resist lithography, people more and more favor the series in negative photoresist SU-8, its absorbance in near-ultraviolet range is low, therefore the exposure uniformity that whole photoresist layer obtains can obtain having the thick film figure of vertical sidewall and high-aspect-ratio.This kind of photoetching compositions at least comprises acid-sensitive epoxy resin, photic acid-producing agent and solvent, and existing bibliographical information is made fiber waveguide device (B.B ê che et al/Optics Communications230 (2004) 91-94) with it.This method is compared with the method for making of traditional polymer optical waveguide, reduced evaporation metal rete, ion etching and removed the processes such as metallic diaphragm, not only can shorten manufacturing process but also can reduce manufacturing cost, the more important thing is and can also obtain the more steep optical waveguide of sidewall.There is patent report to utilize chromophore's doping such as amorphous polycarbonate (APC) and AJL8 to be used for fiber waveguide device (U.S.Pat.No.0297708) as photoelectricity (EO) polymkeric substance.
Directly the photoresist for optical communication field as material of main part also should possess the feature of organic polymer optical waveguide material except can making micro-pattern with ordered structure, as good thermal stability, and low absorption light loss.Tg after common acids sensing epoxy resin series photoresist is crosslinked can reach more than 200 ℃, can meet the demands completely, but larger at the light loss of communication band (1310nm and 1550nm place).Within the scope of 1300～1600nm, absorb the main absorption in over-frequency from molecule, wherein the absorption in over-frequency of C-H, is higher at optical communication window, and the absorption of C-F key is very little.So can increase material at the optical transparence of optical communication wave band after replacing C-H with C-F, reduce absorption loss.
Therefore, the negative photoresist that needs a kind of part or all of fluorine to replace in optical communication field, reduce the making step of traditional polymer optical waveguide, shorten fabrication cycle, can obtain on this basis the polymer optical wave guide of sidewall, surfacing, low light loss.
Summary of the invention
The object of the invention is to provide a kind of negative fluorine-contained photoetching compositions, and it is suitable for the preparation of polymer optical waveguide device.
Negative fluorine-contained photoetching compositions of the present invention is comprised of epoxy-capped fluorine-containing polycarbonate, photic acid-producing agent (light trigger) and organic solvent, by weight with 100% calculating, the content of epoxy-capped fluorine-containing polycarbonate is 38～66wt%, the content of photic acid-producing agent is 8% of epoxy-capped fluorine-containing polycarbonate, and all the other are organic solvent.
This negative fluorine-contained photoetching compositions can be adjusted by changing the kind of photic acid-producing agent the exposure wavelength of photoetching compositions, simultaneously due in the epoxy polycarbonate fluoridizing, part hydrogen atom is replaced by fluorine atom, less in communication band absorption, so this photoetching compositions can expose in the scope of ultraviolet wavelength 200～400nm and polymer optical waveguide device is made in imaging.
Wherein, the structural formula of epoxy-capped fluorine-containing polycarbonate is the compound as shown in (1),
M is 5～25 integer, the integer that n is 0～25, the integer that preferred m is 8～12, the integer that n is 8～12.
Epoxy-capped fluorine-containing polycarbonate shown in structural formula (1), its number-average molecular weight (Mn) can be 2000～10000, and preferably 3000～5000, dispersion degree (Mw/Mn) can be in 1.0～2.0 scopes.Its molecular weight can pass through gel permeation chromatography (GPC) and measure.It is crosslinked to there is open loop in the epoxide group in this polycarbonate under the effect of initiating agent (photic acid-producing agent), the most important thing is that this epoxy-capped fluorine-containing polycarbonate does not absorb (as Fig. 2) at optical communication wave band (1310nm and 1550nm place), has so just guaranteed this kind of absorption light loss that material is lower.
Organic solvent in negative fluorine-contained photoetching compositions is methylene chloride, chloroform, tetrahydrofuran, benzene, toluene, propylene-glycol monoalky lether, propylene glycol alkyl ether acetic acid ester, cyclopentanone, butyl acetate, methyl isobutyl ketone, positive butanone, 2 – pentanones, 4 – Jia Ji – 2 – pentanones, cyclohexanone, 2 – heptanone, γ – butyrolactone, ethylene glycol monoethyl ether acetate, glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, butyrolactone, N, the mixing of one or more in N – dimethyl formamide.When photoetching compositions is coated on substrate for the preparation of polymer optical waveguide device, through front baking organic solvent, can substantially remove.
Photoetching compositions of the present invention comprises at least one photic acid-producing agent, and it can form a kind of acid when exposure, and this kind of acid can be used as the thermal cross-linking agent of epoxy-capped fluorine-containing polycarbonate, makes it crosslinked under the adjusting of heating.The photic acid-producing agent that is applicable to epoxy-capped fluorine-containing polycarbonate of the present invention mainly comprises salt compounded of iodine and sulfosalt etc., triphenyl hexafluoro-antimonic acid sulfosalt for example, triphenyl hexafluorophosphoric acid sulfosalt, triphenyl hexafluoroarsenate sulfosalt, triphenyl tetrafluoro boric acid sulfosalt, 4 – aminomethyl phenyl diphenyl hexafluorophosphoric acid sulfosalts, 4-(thiophenyl) phenyl hexafluorophosphoric acid sulfosalt, diphenyl hexafluoro-antimonic acid salt compounded of iodine, diphenyl hexafluorophosphoric acid salt compounded of iodine, diphenyl hexafluoroarsenate salt compounded of iodine, diphenyl tetrafluoro boric acid salt compounded of iodine, xylyl hexafluoroarsenate salt compounded of iodine, di-tert-butyl-phenyl hexafluorophosphoric acid salt compounded of iodine etc., also can be the potpourri of above-mentioned photic acid-producing agent, and be better than using not the sulfosalt with alkane side chain.
With fluorine-containing photoetching compositions of the present invention, prepare the technique of polymer optical waveguide device and structural representation as shown in Figure 1, its step is as follows:
1) the negative fluorine-contained photoetching compositions of being prepared by the present invention is spin-coated on SiO
2on substrate, according to the thickness of photoresist concentration and spin speed control photoresist coating, be 3～7 μ m;
2) SiO of negative fluorine-contained photoetching compositions will be scribbled
2substrate is front baking 30～60min under 70～110 ℃ of temperature conditions;
3) see through this negative fluorine-contained photoetching compositions coating of waveguide mask plate imaging type uv-exposure of strip structure (10 * 8 μ m), the time shutter is 10～480s, and exposure wavelength is 200～400nm, and luminous power is 800～1200W;
4) after exposure, in this negative fluorine-contained photoetching compositions coating of 100～160 ℃ of lower bakings of temperature conditions;
5) with developer solution, this negative fluorine-contained photoetching compositions coating is developed, development time is 10～30s; Developer solution can be single or mixed type organic solvent, as propylene-glycol monoalky lether, propylene glycol alkyl ether acetic acid ester, cyclopentanone, butyl acetate, methyl isobutyl ketone, positive butanone, 2 – pentanones, 4 – Jia Ji – 2 – pentanones, cyclohexanone, 2 – heptanone, γ – butyrolactone, ethylene glycol monoethyl ether acetate, glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, butyrolactone, N, N – dimethyl formamide etc.;
6) dry after carrying out under 90～160 ℃ of temperature conditions, the time is 30～60min, at SiO
2on substrate, prepare polymer optical waveguide device.
Accompanying drawing explanation
Fig. 1: the part process chart of preparing polymer optical waveguide device of the present invention;
Wherein, each component names is: with SiO
2the silicon substrate 1 of rete, fluorine-containing photoetching compositions coating 2, strip structure waveguide mask plate 3, ultraviolet light 4, polymer optical wave guide 5.
The corresponding step 1) of difference: the fluorine-containing photoetching compositions coating 2 that on substrate 1 prepared by spin coating the present invention; Step 3): the epoxy-capped fluorine-containing polycarbonate photoetching compositions coating through front baking 2 is seen through to mask plate 3 imaging type ultraviolet light 4 exposures of strip structure; Step 6): through middle baking, development, after dry the polymer optical waveguide device preparing after step on substrate 1.
Fig. 2: the near infrared absorption spectrogram of the epoxy-capped fluorine-containing polycarbonate of the embodiment of the present invention 2 preparations;
As can be seen from the figure, the C-F key that in polycarbonate, optical absorption is lower has partly replaced after the c h bond of optical absorption, make this epoxy-capped fluorine-containing polycarbonate absorb very little at 1310nm and 1550nm optical communication wavelength place, can reduce like this absorption light loss of optical waveguide material, thereby for the preparation of polymer optical waveguide device.
Embodiment
Following specific embodiment will be made detailed explanation with regard to the preparation and application of composition of the present invention.But these embodiment are not intended to limit by any way or limit scope of the present invention, should not think that providing unique can put into practice condition of the present invention, parameter or data yet.
Embodiment 1:
The bisphenol-A that 9.00g is fluoridized is dissolved in 40mL pyridine, and ice bath is cooled to 5 ℃, will be dissolved in 60mLCH
2cl
2two (trichloromethyl) carbonic esters (having another name called solid triphosgene) of 2.20g be added dropwise to wherein, under room temperature, react again 6h.Add 5%(v/v) after HCl270mL neutralization reaction liquid, use CH
2cl
2extract 3 times, then with deionized water, wash to take for 5 times and guarantee that organic phase is as neutral.Concentrated organic phase deposits to obtain white precipitate, suction filtration post-drying to 50mL in a large amount of methyl alcohol.Then in product, add epichlorokydrin (50g), after the thawing that heats up, use sodium hydrate solid catalysis, every 0.5h adds 0.25g NaOH, coreaction 5h.After adding, in 60 ℃, keep 6h to complete cyclization.Steam unreacted epichlorokydrin, then use CH
2cl
2extraction, after filtration by CH
2cl
2steaming removes, and obtains can be used for preparing the epoxy-capped fluorine-containing polycarbonate of polymer optical waveguide device, and structure is as follows:
Productive rate is 38.6%, Mn=3945, Mw/Mn=1.32, the integer that m is 10～11.
1H?NMR(500MHz,CDCl
3,TMS):δ(ppm)7.34（1H,s）,7.32(1H,s),6.93(1H,s),6.92(1H,s),4.29-4.26(1H,m),4.00-3.97(1H,m),3.39-3.36(1H,m),2.94-2.93(1H,m),2.79-2.77(1H,m)。
13C?NMR(125MHz,CDCl
3,TMS):δ(ppm)158.66,131.51,126.19,125.96,124.36,114.15,68.80,63.56,49.99,44.62。
19F?NMR(470MHz,CDCl
3,CFCl
3):δ(ppm)-64.17(1F,s)。IR (KBr, cm
-1): γ (epoxide group)=930.0, γ (C
aromatic group)=1612.0 and 1514.5, γ (C-F)=1126～1300.This resin is very little in the absorption of optical communication wave band (1310 and 1550nm), as Fig. 2.
Embodiment 2:
By 8.07g(24mmol) bisphenol-A and the 1.61g(6mmol that fluoridize) bisphenol Z is dissolved in 45mL pyridine, and ice bath is cooled to 0 ℃, will be dissolved in 70mL CH
2cl
2two (trichloromethyl) carbonic esters (having another name called solid triphosgene) of 2.47g be added dropwise to wherein, under room temperature, react again 6h.Add 5%(v/v) after HCl300mL neutralization reaction liquid, use CH
2cl
2extract 3 times, then with deionized water, wash to take for 5 times and guarantee that organic phase is as neutral.Concentrated organic phase deposits to obtain white precipitate, suction filtration post-drying to 40mL in a large amount of methyl alcohol.Then in product, add epichlorokydrin (50g), after the thawing that heats up, use sodium hydrate solid catalysis, every 0.5h adds 0.25g NaOH, coreaction 5h.After adding, in 60 ℃, keep 6h to complete cyclization.Steam unreacted epichlorokydrin, then use CH
2cl
2extraction, after filtration by CH
2cl
2steaming removes, and obtains can be used for preparing the epoxy-capped fluorine-containing polycarbonate of polymer optical waveguide device, and structure is as follows:
Productive rate is 45.8%, Mn=4179, Mw/Mn=1.59, the integer that m is 8～9, the integer that n is 2～3.
1H?NMR(500MHz,CDCl
3,TMS):δ(ppm)7.35-7.33（1H,t）,7.20-7.19(1H,t),6.94-6.93(1H,t),6.86-6.84(1H,t),4.30-4.27(1H,m),4.01-3.98(1H,m),3.40-3.38(1H,m),2.95-2.93(1H,m),2.79-2.78(1H,m),2.24-2.23(1H,t),1.57-1.51(1H,m)。
13C?NMR(125MHz,CDCl
3,TMS):δ(ppm)158.67,158.15,156.12,153.64,141.61,131.52,128.17,126.49,126.25,124.31,114.16,68.80,63.56,50.00,45.11,44.66,37.39,26.40,22.91。
19F?NMR(470MHz,CDCl
3,CFCl
3):δ(ppm)-63.85(1F,s)。IR (KBr, cm
-1): γ (epoxide group)=830.0, γ (C
aromatic group)=1610.9, γ (C-F)=1126～1300, γ (hexatomic ring)=1513.1 and 2399.2.
Embodiment 3:
The epoxy-capped fluorine-containing polycarbonate of 2.800g (is made by method in embodiment 1, Mn=3945, Mw/Mn=1.32 or make by method in embodiment 2, Mn=4179, Mw/Mn=1.59), the epoxy-capped fluorine-containing polycarbonate quality of triphenyl hexafluorophosphoric acid sulfosalt 0.204g(8%) and 4.000g cyclopentanone mix, this solution is filtered and obtains photoetching compositions solution (solid content is about 40%) with the filtrator of 0.22 μ m respectively.
The silicon chip H of silica coating will be scribbled
2sO
4(98wt%): H
2o
2the solution-treated of=7:3, then distinguishes the above-mentioned photoetching compositions solution of spin coating, and rotating speed is 500rpm, 9s, 2000rps, 30s, photoresist film bed thickness approximately 3 μ m; Front baking 30min at 95 ℃; Uv-exposure 8min(1000W, 300～400nm); After at 120 ℃, dry 1h, obtained transparent optical thin film, surfaceness is respectively 0.354nm and 0.311nm(3 * 3 μ m).
Embodiment 4:
The epoxy-capped fluorine-containing polycarbonate of 2.800g (is made by method in embodiment 1, Mn=3945, Mw/Mn=1.32 or make by method in embodiment 2, Mn=4179, Mw/Mn=1.59), the epoxy-capped fluorine-containing polycarbonate quality of triphenyl hexafluorophosphoric acid sulfosalt 0.204g(8%) and 1.300g cyclopentanone mix, this solution is filtered and obtains photoetching compositions solution (solid content is about 65%) with the filtrator of 0.22 μ m respectively.
The silicon chip H of silica coating will be scribbled
2sO
4(98wt%): H
2o
2the solution-treated of=7:3, then distinguishes the above-mentioned photoetching compositions solution of spin coating, and rotating speed is 500rpm, 9s, 2000rps, 30s, photoresist film bed thickness approximately 7 μ m; Front baking 50min at 95 ℃; Uv-exposure 8min(1000W, 300～400nm); After at 120 ℃, dry 1h, obtained transparent optical thin film, surfaceness is respectively 0.364nm and 0.332nm(3 * 3 μ m).
Embodiment 5:
The epoxy-capped fluorine-containing polycarbonate of 2.800g (is made by method in embodiment 1, Mn=3945, Mw/Mn=1.32 or make by method in embodiment 2, Mn=4179, Mw/Mn=1.59), the epoxy-capped fluorine-containing polycarbonate quality of diphenyl hexafluorophosphoric acid salt compounded of iodine 0.204g(8%) and 4.000g cyclopentanone mix, this solution is filtered and obtains photoetching compositions solution (solid content is about 40%) with the filtrator of 0.22 μ m respectively.
The silicon chip H of silica coating will be scribbled
2sO
4(98wt%): H
2o
2the solution-treated of=7:3, then distinguishes the above-mentioned photoetching compositions solution of spin coating, and rotating speed is 500rpm, 9s, 2000rps, 30s, photoresist film bed thickness approximately 3 μ m; Front baking 30min at 95 ℃; Uv-exposure 8min(1000W, 200～300nm); After at 120 ℃, dry 1h, obtained transparent optical thin film, surfaceness is respectively 0.362nm and 0.301nm(3 * 3 μ m).
Embodiment 6:
The epoxy-capped fluorine-containing polycarbonate of 2.800g (is made by method in embodiment 1, Mn=3945, Mw/Mn=1.32 or make by method in embodiment 2, Mn=4179, Mw/Mn=1.59), the epoxy-capped fluorine-containing polycarbonate quality of diphenyl hexafluorophosphoric acid salt compounded of iodine 0.204g(8%) and 1.300g cyclopentanone mix, this solution is filtered and obtains photoetching compositions solution (solid content is about 65%) with the filtrator of 0.22 μ m respectively.
The silicon chip H of silica coating will be scribbled
2sO
4(98wt%): H
2o
2the solution-treated of=7:3, then distinguishes this photoetching compositions solution of spin coating, and rotating speed is 500rpm, 9s, 2000rps, 30s, photoresist film bed thickness approximately 7 μ m; Front baking 50min at 95 ℃; Uv-exposure 8min(1000W, 200～300nm); After at 120 ℃, dry 1h, obtained transparent optical thin film, surfaceness is respectively 0.371nm and 0.328nm(3 * 3 μ m).
Embodiment 7:
The silicon chip H of silica coating will be scribbled
2sO
4(98wt%): H
2o
2the solution-treated of=7:3, then distinguishes spin coating photoetching compositions solution (embodiment 3～6 gained), and rotating speed is 500rpm, 9s, and 2000rps, 30s, photoresist film bed thickness is 5 μ m; At 95 ℃, dry 40min; Mask (slab waveguide mask plate, 10 * 8 μ m) uv-exposure 8min(1000W, 200～300nm); At 120 ℃, dry 1h; 30s develops in ethylene glycol monomethyl ether acetate; At 130 ℃ of temperature, dry 1h, can make respectively polymkeric substance straight wave guide device.And record under 1550nm wavelength, 10 * 8 μ m straight wave guide bar light loss intercept method test light losses are respectively 0.23,0.19,0.25,0.21dB/cm.
Claims (5)
1. a negative fluorine-contained photoetching compositions, it is characterized in that: by epoxy-capped fluorine-containing polycarbonate, photic acid-producing agent and organic solvent, formed, by weight with 100% calculating, the content of epoxy-capped fluorine-containing polycarbonate is 38～66wt%, the content of photic acid-producing agent is 8% of epoxy-capped fluorine-containing polycarbonate, and all the other are organic solvent; The structural formula of epoxy-capped fluorine-containing polycarbonate as shown in (1),
M is 5～25 integer, the integer that n is 0～25; Photic acid-producing agent is sulfosalt or salt compounded of iodine.
2. a kind of negative fluorine-contained photoetching compositions as claimed in claim 1, is characterized in that: the integer that in epoxy-capped fluorine-containing polycarbonate structure formula, m is 8～12, the integer that n is 8～12.
3. a kind of negative fluorine-contained photoetching compositions as claimed in claim 1, it is characterized in that: organic solvent is methylene chloride, chloroform, tetrahydrofuran, benzene, toluene, propylene-glycol monoalky lether, propylene glycol alkyl ether acetic acid ester, cyclopentanone, butyl acetate, methyl isobutyl ketone, positive butanone, 2 – pentanones, 4 – Jia Ji – 2 – pentanones, cyclohexanone, 2 – heptanone, γ – butyrolactone, ethylene glycol monoethyl ether acetate, glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, butyrolactone, N, the mixing of one or more in N – dimethyl formamide.
4. a kind of negative fluorine-contained photoetching compositions as claimed in claim 1, it is characterized in that: photic acid-producing agent is triphenyl hexafluoro-antimonic acid sulfosalt, triphenyl hexafluorophosphoric acid sulfosalt, triphenyl hexafluoroarsenate sulfosalt, triphenyl tetrafluoro boric acid sulfosalt, 4 – aminomethyl phenyl diphenyl hexafluorophosphoric acid sulfosalts, 4-(thiophenyl) phenyl hexafluorophosphoric acid sulfosalt, diphenyl hexafluoro-antimonic acid salt compounded of iodine, diphenyl hexafluorophosphoric acid salt compounded of iodine, diphenyl hexafluoroarsenate salt compounded of iodine, diphenyl tetrafluoro boric acid salt compounded of iodine, xylyl hexafluoroarsenate salt compounded of iodine, the mixing of one or more in di-tert-butyl-phenyl hexafluorophosphoric acid salt compounded of iodine.
5. the application of the negative fluorine-contained photoetching compositions of claim 1～4 described in any one in preparing polymer optical waveguide device.
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| CN106406029A (en) * | 2016-09-09 | 2017-02-15 | 吉林大学 | Negative fluorine-containing polycarbonate photoresist composition and application for preparing optical switch |
| CN108440934A (en) * | 2018-04-27 | 2018-08-24 | 刘凤宇 | A kind of preparation method of optical waveguide new material |
| CN111253563A (en) * | 2020-01-14 | 2020-06-09 | 浙江大学 | Application of polycarbonate as ultraviolet photoresist material |
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