CN1272365C - Process for preparing water base developing photosensitive polyimide material - Google Patents
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Abstract
本发明属于一种水基显影光敏聚酰亚胺材料的制备方法。采用芳香二酯二酰氯同3，5-二胺基苯甲酸、4，4’-二胺基3，3’-二羟基二苯甲烷以及4，4’-二胺基3，3’-二羟基二苯砜等单体聚合，生成聚酰亚胺预聚物——聚酰胺酸酯，特性粘度在0.35-0.50范围内，加入2-重氮萘醌衍生物(NQD)为光敏剂，使之成为具有很高的感光性能和很好的成膜性以及耐热性能的光敏材料。The invention belongs to a preparation method of a water-based developing photosensitive polyimide material. Using aromatic diester diacid chloride with 3,5-diaminobenzoic acid, 4,4'-diamino 3,3'-dihydroxydiphenylmethane and 4,4'-diamino 3,3'-di Polymerization of monomers such as hydroxydiphenyl sulfone to generate polyimide prepolymer - polyamic acid ester, the intrinsic viscosity is in the range of 0.35-0.50, adding 2-naphthoquinone diazide derivatives (NQD) as photosensitizer, so that It has become a photosensitive material with high photosensitive performance, good film-forming property and heat resistance.
Description
Technical field
The invention belongs to the preparation method of water base developing photosensitive polyimide material.
Background technology
Polyimide is an opportunity with buffer coating (Buffer Coat) mould material of being LSI, has established the status at electronic applications.The buffer coating film is except that the Alpha-ray effect of shielding, and the packaging process of installing at resin embedding and lead frame also the LSI chip is heated and mechanical shock shields.The chip of LSI sticks with glue agent with on its lead frame of packing into after making monolithic, at this moment will stand 300 ℃, the condition of 30MPa.Tackiness agent used herein mostly is polyimide.Potting resin is generally through injection molding, and processing conditions at this moment is 180 ℃, 300MPa.This just requires buffer coating can bear this heat and mechanical shock, does not up to the present also use the report of polyimide other resin in addition.
The buffer coating film forms all surfaces that the back covers silicon chip at silicon chip, adopt etching method to make the wiring diagram that electrode is partly exposed.Etching solution is a hydrazine hydrate, because this etching is isotropic, can not get resolution, will form alkali proof photoresist material as mask on buffer coating, washes the technology more complicated after the etching again.After photo-sensistive polyimide resin is used, manufacturing procedure is simplified greatly, almost all use photo-sensistive polyimide as buffer coating at present.
Photo-sensistive polyimide is the same with photoresist material to be divided into minus (cross-linking type) and the photosensitive eurymeric that is partly dissolved (change in polarity type) that photosensitive part stays.The negative type photo-sensitive polyimide of early development has covalent bond type of linking agent being introduced with the polyamic acid ester-formin and the ionic of introducing linking agent with the polyamic acid salt form.General covalent type has better resolution than ionic, but requires to carry out under the atmosphere of certain oxygen concn during imidization.The production of minus light-sensitive polyimide mainly concentrates on Japan-US a few company, as toray, Dupont etc.The positive type photosensitive polyimide was reported first at the end of the eighties, and the design of positive type photosensitive polyimide is more much more difficult than minus.Along with the raising of integrated level and the speed of LSI, the interval of electrode narrows down, and this just requires photo-sensistive polyimide that higher resolution is arranged.The developing solution of the light-sensitive polyimide of minus is an organic solvent, has some problem aspect environment.The eurymeric of exploitation is improved largely than minus resolution now, and developing solution also adopts and the general identical environment-friendly type tetramethylammonium hydroxide aqueous solution of photoresist material, and the positive type photosensitive polyimide will become the main flow of buffer coating gradually from now on.
Exercise question is " in the document of A novel photosensitive polyimide:a polyimidecontaining the hydroxytriphenyamine structure withdiazonaphthoquinone (Satoshi Akimoto et al.High Perform.Polym.12 (2000) 177-184); the dianhydride that the author will be contained hexafluoro prepares the water base developing photoresist material as the synthetic light-sensitive polyimide of structure monomer, and film comes off when alkaline development easily.
At exercise question is in the document of " Positive-type photosensitive polyimide precursorcomposition " (the Masao Tomikawa et el. patent No. is US6524764B1), the author becomes polyamic acid with dianhydride with the diamines direct polymerization, use the imidization of chemical imidization method part again, be unfavorable for controlling the imidization degree like this, the glue poor stability.
In the Chinese patent CN1227637A that is entitled as " containing 2, the positive photoresist composition of 4-dinitrobenzene-1-naphthols ", use be resol, although the very high thermotolerance of light sensitivity is very poor.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of water base developing photosensitive polyimide material.
The present invention adopts the aromatic diesters diacid chloride with 3,5-diamines yl benzoic acid, 4,4 '-two amidos 3,3 '-dioxydiphenyl methane and 4,4 '-two amidos 3, monomer polymerizations such as 3 '-dihydroxy diphenylsulphone, generate polyimide preformed polymer---poly amic acid ester, limiting viscosity is in the 0.35-0.50 scope, and adding 2-diazo naphthoquinone derivative (NQD) is photosensitizers, makes it to become the photochromics with very high photosensitive property and good film-forming properties and resistance toheat.
The exposure principle is exactly that the polyimide photoresist material that will contain 2-diazo naphthoquinone derivative exposes under 365nm (i line)～436nm (g line) UV-light, 2-diazo naphthoquinone derivative (NQD) is decomposed into the indenes acid derivative, this analog derivative can be dissolved in the alkaline aqueous solutions such as tetramethylphosphonihydroxide hydroxide amine, like this, exposed portion can be dissolved in the above-mentioned weak base, unexposed part is not dissolved in above-mentioned weak base, forms positive glue pattern.
Synthetic water base developing light-sensitive polyimide of the present invention has following array structure
Ar1=aromatic diamine A residue wherein, Ar2=aromatic diamine B residue, Ar3=aromatic series dianhydride residue, n, m are the integer greater than 15;
The present invention adopts following component to synthesize water-based development light-sensitive polyimide photoresist material:
(1) dianhydride: 4,4 '-(the different trimethylene base of hexafluoro) dibenzoic acid acid anhydride (6FDA), 3,3 ', 4,4 '-hexichol benzophenone tetracarboxylic dianhydride (BTDA), 3,3 ', 4,4 '-BPDA (BPDA), 3,3 ', 4,4 '-triphen diether tetracarboxylic dianhydride (HQDPA), 3,3 ', 4, wherein a kind of of 4 '-phenyl ether tetracarboxylic dianhydride (ODPA) or pyromellitic acid dianhydride (PMDA) or two kinds;
(2) aromatic diamine A:2, and 2-(3,3 '-dihydroxyl 4,4 '-diamino) diphenyl propane (HDMMDA), 3,3 '-dihydroxyl 4,4 '-benzidine (HOTOL), 3,3 '-dihydroxyl 4,4 '-diaminodiphenylsulfone(DDS) (HDDS), 3,5-diamines yl benzoic acid (3,5-DABA), 2,4-diaminophenol or 2,2-(3,3 '-dihydroxyl 4,4 '-diamino) phenylbenzene hexafluoorpropane (HD6FDA);
(3) aromatic diamine B: ether diamine (ODA), 2,2-(4,4 '-diamino) diphenyl propane (DMMDA), 4,4 '-benzidine (OTOL), 4,4 '-diaminodiphenylsulfone(DDS) (4,4 '-DDS), 3,3 '-diaminodiphenylsulfone(DDS) (3,3 '-DDS), mphenylenediamine (m-DA), Ursol D (p-DA) or 4,4 '-diaminodiphenyl-methane (MDA);
These aromatic diamines A can use separately, also can be to mix use with aromatic diamine B;
(4) esterifying agent: wherein a kind of of methyl alcohol, ethanol, propyl alcohol, Virahol or butanols or two kinds;
The alkaline aqueous solution of (5) development usefulness is: the tetramethylphosphonihydroxide hydroxide amine aqueous solution, and aqueous sodium carbonate or aqueous sodium hydroxide solution, concentration expressed in percentage by weight is between 0.1-2.4%;
(6) photosensitizers:
Wherein D is 1-naphthoquinones 2-nitrine 5-alkylsulfonyl or 1-naphthoquinones 2-nitrine 4-alkylsulfonyl
(7) solvent: pimelinketone, gamma-butyrolactone, N-Methyl pyrrolidone, N,N-DIMETHYLACETAMIDE, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether vinyl acetic monomer or ethylene glycol monoethyl ether vinyl acetic monomer, wherein one or two or more kinds mixed use;
Technological process is as follows: at first with dianhydride and esterifying agent, mol ratio is 1: the 1.9-2.0 reaction generated the diester diacid in 8-10 hour, then, in this diester diacid, add the chloride reagent of 2-2.5 mole, reacted 5-6 hour, at low temperature-10 ℃---25 ℃ of addings and the equimolar diamine reactant 8-10 of dianhydride hour, again this resin is sunk in the ethanol, filter, embathe 2-3 time seasoning with deionized water and dehydrated alcohol; Dried resin is dissolved in the solvent again, volume ratio is in 2: 1 the mixed solvent, be made into 15～25% polyamic acid resin solution, the NQD derivative that adds 10-30% then, again this resin solution is coated on the polished silicon slice, dry 20-30min under 60-80 ℃, under 365nm (i line)～436nm (g line) UV-light, expose, in concentration is tetramethylphosphonihydroxide hydroxide amine aqueous solution or aqueous sodium carbonate or the aqueous sodium hydroxide solution development of 0.1-2.4%, use rinsed with deionized water, and then dry by the fire 30-60min after 250-360 ℃, obtain good photoresist film.
Embodiment is as follows:
Embodiment 1
Purified 6.44gBTDA (0.020 mole) is dissolved in the 25mlN N,N-DIMETHYLACETAMIDE, stir and add 1.28g methyl alcohol (0.040 mole) down, at room temperature react 8hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 5hr again, a ℃ adding 5.21HDMMDA (0.020 mole) obtains polyamic acid resin solution at low temperature-10.
Above-mentioned polyamic acid resin is sunk in the ethanol, filter, embathe 2 times seasoning with deionized water and dehydrated alcohol.Again will be the dried resin volume ratio that is dissolved in N-Methyl pyrrolidone/gamma-butyrolactone be in 2: 1 the mixed solvent, add NQD-I derivative 1.5g and be made into 20% polyamic acid resin solution.
Above-mentioned polyamic acid resin solution is applied to spin-coating method on the silicon chip of polishing, dry 20min under 80 ℃, the 4min that then exposes under 365nm (i line)～436nm (g line) UV-light develops at 1% tetramethylphosphonihydroxide hydroxide amine aqueous solution, uses rinsed with deionized water.
Embodiment 2
To make with extra care 5.88gBPDA (0.02 mole) is dissolved in the 36ml N,N-DIMETHYLACETAMIDE, stir and add 1.84g ethanol (0.04 mole) down, at room temperature react 10hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-15 ℃ adding 2.44gHOTOL (0.01 mole) and 2.00gODA (0.01 mole), reaction 5hr obtains polyamic acid resin solution.
Above-mentioned polyamic acid resin is sunk in the ethanol, filter, embathe 3 times seasoning with deionized water and dehydrated alcohol.Again will be the dried resin volume ratio that is dissolved in N-Methyl pyrrolidone/ethylene glycol monobutyl ether be in 2: 1 the mixed solvent, add NQD-II derivative 1.8g and be made into 20% polyamic acid resin solution
Above-mentioned polyamic acid resin solution is applied to spin-coating method on the silicon chip of polishing, dry 20min under 80 ℃, 4min then exposes under 365nm (i line)～436nm (g line) UV-light.Develop at 2.4% tetramethylphosphonihydroxide hydroxide amine aqueous solution, use rinsed with deionized water.
Embodiment 3
Purified 3.6gPMDA (0.020 mole) is dissolved in the 70mlN-methyl-2-pyrrolidone, stir and add 2.40g propyl alcohol (0.040 mole) down, at room temperature react 8hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-20 ℃ adding 2.44gHOTOL (0.01 mole) and 2.00gODA (0.01 mole), reaction 5hr obtains polyamic acid resin solution.
Above-mentioned polyamic acid resin is sunk in the ethanol, filter, embathe 3 times seasoning with deionized water and dehydrated alcohol.Again will be the dried resin volume ratio that is dissolved in N-Methyl pyrrolidone/ethylene glycol monobutyl ether be in 2: 1 the mixed solvent, add NQD-III derivative 1.4g and be made into 20% polyamic acid resin solution
Above-mentioned polyamic acid resin solution is applied to spin-coating method on the silicon chip of polishing, dry 20min under 80 ℃, 4min then exposes under 365nm (i line)～436nm (g line) UV-light.Develop at 2% tetramethylphosphonihydroxide hydroxide amine aqueous solution, use rinsed with deionized water.
Embodiment 4
Purified 8.05gHQDPA (0.020 mole) is dissolved in the 26mlN-methyl-2-pyrrolidone, stir and add 2.40g Virahol (0.040 mole) down, at room temperature react 8hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-25 ℃ adding 3.66gHD6FDA (0.01 mole) and 2.48g4,4 '-DDS (0.01 mole) reacts 5hr and obtains polyamic acid resin solution.
Above-mentioned polyamic acid resin is sunk in the ethanol, filter, embathe 3 times seasoning with deionized water and dehydrated alcohol.Again will be the dried resin volume ratio that is dissolved in N-Methyl pyrrolidone/ethylene glycol monobutyl ether be in 2: 1 the mixed solvent, add NQD-III derivative 1.4g and be made into 20% polyamic acid resin solution
Above-mentioned polyamic acid resin solution is applied on the silicon chip of polishing dry 20min under 80 ℃, then exposure 4min under 365nm (i line)～436nm (g line) ultraviolet source with spin-coating method.Develop at 2% aqueous sodium carbonate, use rinsed with deionized water.
Embodiment 5
Purified 8.05gODPA (0.020 mole) is dissolved in the 26mlN-methyl-2-pyrrolidone, stir and add 2.96g butanols (0.040 mole) down, at room temperature react 10hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-25 ℃ adding 1.52g3,5-DABA (0.01 mole) and 2.48g4,4 '-DDS (0.01 mole), reaction 5hr obtains polyamic acid resin solution.
Above-mentioned polyamic acid resin is sunk in the ethanol, filter, embathe 3 times seasoning with deionized water and dehydrated alcohol.Again will be the dried resin volume ratio that is dissolved in N-Methyl pyrrolidone/ethylene glycol monobutyl ether be in 2: 1 the mixed solvent, add NQD-IV derivative 2.2g and be made into 20% polyamic acid resin solution
Above-mentioned polyamic acid resin solution is applied to spin-coating method on the silicon chip of polishing, dry 20min under 80 ℃, 4min then exposes under 365nm (i line)～436nm (g line) UV-light.Develop at 0.5% aqueous sodium hydroxide solution, use rinsed with deionized water.
Embodiment 6
Purified 8.92g6FDA (0.020 mole) is dissolved in the 25mlN-methyl-2-pyrrolidone, stir and add 2.96g butanols (0.040 mole) down, at room temperature react 8hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-15 ℃ adding 1.52g3,5-DABA (0.01 mole) and 2.00gODA (0.01 mole) react 5hr and obtain polyamic acid resin solution.All the other experiment conditions are with embodiment 5.
Embodiment 7
Purified 3.22gBTDA (0.020 mole) is dissolved in the 20mlN-methyl-2-pyrrolidone, stir and add 2.40g Virahol (0.040 mole) down, at room temperature react 8hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-20 ℃ adding 3.66gHD6FDA (0.01 mole) and 2.48g4,4 '-DDS (0.01 mole) reacts 5hr and obtains polyamic acid resin solution.All the other experiment conditions are with embodiment 4.
Embodiment 8
Purified 5.88gBPDA (0.020 mole) is dissolved in the 30mlN-methyl-2-pyrrolidone, stir and add 1.84g ethanol (0.04 mole) down, at room temperature react 10hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-25 ℃ adding 2.44gHOTOL (0.01 mole) and 2.00gODA (0.01 mole), reaction 5hr obtains polyamic acid resin solution.All the other experiment conditions are with embodiment 1.
Embodiment 9
Purified 4.36gPMDA (0.020 mole) is dissolved in the 15ml N,N-DIMETHYLACETAMIDE, stir and add 1.84g ethanol (0.04 mole) down, at room temperature react 10hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-10 ℃ ℃ adding 1.95gHOTOL (0.008 mole) and 2.98g3,3 '-DDS (0.012 mole) reacts 5hr and obtains polyamic acid resin solution.
Except that " be made into 20% polyamic acid resin solution " among the embodiment 1 being changed into " be made into 15% polyamic acid resin solution ", all the other experiment conditions are with embodiment 1.
Embodiment 10
Purified 8.05gHQDPA (0.020 mole) is dissolved in the 15mlN-methyl-2-pyrrolidone, stir and add 2.96g butanols (0.040 mole) down, at room temperature react 8hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-20 ℃ adding 1.52g3,5-DABA (0.01 mole) and 2.00gODA (0.01 mole) react 5hr and obtain polyamic acid resin solution.All the other experiment conditions are with embodiment 5.
Embodiment 11
In the molten 25ml N,N-DIMETHYLACETAMIDE of purified 8.80g6FDA (0.020 mole), stir and add 2.40g propyl alcohol (0.040 mole) down, at room temperature react 8hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-25 ℃ adding 2.44gHOTOL (0.01 mole) and 2.00gODA (0.01 mole), reaction 5hr obtains polyamic acid resin solution.All the other experiment conditions are with embodiment 3.
Embodiment 12
Purified 6.44gBTDA (0.020 mmole) is dissolved in the 25mlN-methyl-2-pyrrolidone, stir and add 2.96g butanols (0.040 mole) down, at room temperature react 8hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-10 ℃ adding 1.52g3,5-DABA (0.01 mole) and 2.00gODA (0.01 mole) react 5hr and obtain polyamic acid resin solution.All the other experiment conditions are with embodiment 5.
Embodiment 13
Purified 6.20gODPA (0.020 mole) and 1.1gPMDA (5 mmole) are dissolved in the 20ml N,N-DIMETHYLACETAMIDE, stir and add 2.96g butanols (0.040 mole) down, at room temperature react 8hr, add purified thionyl chloride 4.76g (0.040 mole) again, at room temperature react 6hr again, then at low temperature-15 ℃ adding 1.52g3,5-DABA (0.01 mole) and 2.00gODA (0.01 mole) react 5hr and obtain polyamic acid resin solution.Be changed to " adding the NQD-V derivative " except that will " adding the NQD-IV derivative ", all the other experiment conditions are with embodiment 5.
Embodiment 14
Purified 4.36gPMDA (0.020 mole) is dissolved in the 15mlN-methyl-2-pyrrolidone, be changed to outside " adding 1.56g HDMMDA (0.006 mole) and 3.48g4; 4 '-DDS (0.014 mole) " except that will " adding 3.66gHD6FDA (0.01 mole) and 2.48g4; 4 '-DDS (0.01 mole) ", all the other experiment conditions are with embodiment 7.
Embodiment 15
Purified 6.44gBTDA (0.020 mole) is dissolved in the 15ml N,N-DIMETHYLACETAMIDE, be changed to outside " adding 4.89g HOTOL (0.020 mole) " except that will " adding 1.52g3; 5-DABA (0.01 mole) and 2.00gODA (0.01 mole) ", all the other experiment conditions are with embodiment 13.
Embodiment 16
Purified 4.02gHQDPA (0.010 mole) and 2.94gBPDA (0.010 mole) are dissolved in the 25mlN-methyl-2-pyrrolidone, stir adding 2.96g butanols (0.040 mole) down, all the other experiment conditions are with embodiment 3.
Embodiment 17
Purified 4.02gHQDPA (0.010 mole) and 2.94gBPDA (0.010 mole) are dissolved in the 20mlN-methyl-2-pyrrolidone, stir and add 1.48g butanols (0.020 mole) and 0.64g methyl alcohol (0.020 mole) down, at room temperature react 9hr, all the other experiment conditions are with embodiment 1.
Measure the photoetching degree and the thermostability of embodiment 1～17 photoresist film.Here, by electron microscope observation photoetching degree.Thermostability is to measure like this: temperature is elevated to 300 ℃, reduces to room temperature thereafter again, then the deformation extent by the submicroscopy film pattern.
Measurement result is: in embodiment 1～17, be used in the 4min that exposes under 365nm (i line)～436nm (g line) ultraviolet source and can obtain good litho pattern.
The invention has the advantages that photosensitive resin is easy to get, the polyimide resin glue of preparation has well photosensitive property.
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| CN101555318B (en) * | 2009-05-22 | 2011-08-10 | 北京化工大学 | Water-soluble negative light-sensitive polyamic acid salt as well as a preparation method and a developing method thereof |
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