CN104387523A - Film-forming resin containing sesquiterpene lactone and positive dry exposure 193-nanometer photoresist thereof - Google Patents

Film-forming resin containing sesquiterpene lactone and positive dry exposure 193-nanometer photoresist thereof Download PDF

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CN104387523A
CN104387523A CN201410684392.8A CN201410684392A CN104387523A CN 104387523 A CN104387523 A CN 104387523A CN 201410684392 A CN201410684392 A CN 201410684392A CN 104387523 A CN104387523 A CN 104387523A
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film
forming resin
sesquiterpene lactones
general formula
sulfonic acid
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CN104387523B (en
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冉瑞成
沈吉
孙友松
潘新刚
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KUNSHAN SD PHOTOELECTRIC MATERIAL Co Ltd
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KUNSHAN SD PHOTOELECTRIC MATERIAL Co Ltd
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Abstract

The invention discloses a film-forming resin containing sesquiterpene lactone and a positive dry exposure 193-nanometer photoresist thereof. The film-forming resin is prepared from a comonomer which at least comprises the sesquiterpene lactone in a solvent through copolymerization reaction under the condition of the presence of a radical initiator. The film-forming resin is characterized in that the molecular weight of the film-forming resin is 4,000-1,000,000, and the molecular weight distribution of the film-forming resin is 1.4-2.4; and the comonomer mainly comprises the following compounds in percentage by weight: 10%-60% of composition units containing the natural product sesquiterpene lactone, 5%-40% of monomers containing acid-sensitive groups and 1%-20% of other property regulating component monomers. The film-forming resin containing the sesquiterpene lactone and the positive dry exposure 193-nanometer photoresist thereof, which are disclosed by the invention, have good resolution and can be used for enhancing the adhesion property between a photoresist and a silicon slice, enhancing the heat resistant property of the photoresist, improving the etching resistant property of the photoresist and preventing the situations that a photoetching image is influenced and an expensive exposure machine lens is damaged by forming gas overflow from being generated.

Description

Containing sesquiterpene lactones film-forming resin and positivity dry method exposure 193nm photoresist material thereof
Technical field
The present invention relates to a kind of containing natural sesquiterpene lactone copolymers film-forming resin and utilize this film-forming resin formulated for dry method exposure deep ultraviolet (DUV) the positivity chemical amplification type photoetching compositions that is exposure light source with ArF laser (193nm).
Background technology
Photoresist material is the key function material carrying out photoetching process in large-scale integrated circuit industry.What start the nineties in last century to grow up is exposure light source with ArF laser (193nm) deep ultraviolet (DUV) wave band exposure technology is widely used in manufacturing in large-scale integrated circuit, and its resolving power can reach 0.13 ~ 0.10 micrometer range.At present, because exposure sources is constantly updated, updating of technological innovation and photoresist material, resolving power improves constantly, and can reach 0.065 micron.Due to the continuous improvement with photoetching process that improves constantly of resolving power, as the photoresist material of the functional materials of Graphic transitions also in continuous development and improvement.Following technical problem is there is at present: the adhesivity of (1) photoresist material and base material silicon chip is weak in actual process; (2) thermotolerance of photoresist material and etch resistant poor performance; On the other hand, as everyone knows, China's natural product aboundresources, turps, rosin, by leaf-alcohol, terpene and the wide material sources such as sesquiterpene and lactone thereof, output is huge.As pine tree, cypress, all contains the compounds such as high turps, rosin, sesquiterpene and lactone thereof in the trees such as eucalyptus and many herbaceous plant.
How in conjunction with national conditions, by the compound from natural product, be applied to photoresist material field in integrated circuit industry, and above-mentioned technical problem can be overcome simultaneously, solve existing photoresist material to the detrimentally affect of exposure machine camera lens, become the direction that those skilled in the art make great efforts.
Summary of the invention
The present invention's first object is to provide a kind of containing sesquiterpene lactones film-forming resin, and this can increase the adhesive property between photoresist film and silicon chip containing sesquiterpene lactones film-forming resin; Due to the increase of the carbon atom density of film-forming resin, also the resistance toheat of photoresist material will be improved, greatly improve its anti-etching performance, and form gas overflowing when avoiding exposing and affect litho pattern and the situation damaging expensive exposure machine camera lens, further contrast gradient and craft precision.
Second object of the present invention is to provide a kind ofly applies the above-mentioned positivity dry method exposure 193nm photoresist material made containing sesquiterpene lactones film-forming resin.
For reaching above-mentioned first goal of the invention, the technical solution used in the present invention is: a kind of containing sesquiterpene lactones film-forming resin, it is characterized in that: film-forming resin by comonomer, is carried out copolyreaction in a solvent and is prepared under radical initiator existent condition; It is characterized in that: the molecular weight of described film-forming resin is 4,000 ~ 1,000,000, molecular weight distribution is 1.4 ~ 2.4; Described comonomer is mainly the compound of following masses percentage composition:
Containing the component units 10% ~ 60% of natural product sesquiterpene;
Containing acid-labile group monomer 5% ~ 40%;
Other property regulation constituent monomers 1% ~ 20%;
Technique scheme is described as follows:
1. in such scheme, described containing sesquiterpene lactones unit refer to meet chemical general formula ( ) (methyl) acrylic ester compound of at least one sesquiterpene lactones alcohol;
(II);
Described chemical general formula ( ) in the common sesquiterpene lactones alcohol of R base as shown in table 1 below:
Table 1
The described sesquiterpene lactones component units that contains generally is synthesized by the esterification of sesquiterpene lactones alcohol with (methyl) vinylformic acid (or acrylate chloride); Its ethylenic first can be converted into alcohol of formula and carry out above-mentioned esterification again.As:
Described containing acid-labile group monomer be meet chemical general formula ( ) and ( ) at least one compound:
);
Chemical general formula ( ) R in formula 2for H or CH 3;
Chemical general formula ( ) R in formula 3for can leavings group, can one of the optional substituents group of leavings group, as shown in (IV):
(IV);
Wherein Y=-CH 3or-CH 2cH 3.
2., in such scheme, described initiator is the radical initiator of azo initiator, superoxide; Described azo initiator is that azo two isobutyl is fine or azo two is fine for different heptan, and the radical initiator of described superoxide is tert-butyl hydroperoxide pivalate, tertbutyl peroxide, phenylformic acid hydrogen peroxide or benzoyl peroxide etc.; Described initiator amount is 0.3% ~ 15% of described comonomer gross weight.
For reaching above-mentioned second goal of the invention, the technical solution used in the present invention is: a kind of application rights requires the positivity dry method exposure 193nm photoresist material be mixed with containing sesquiterpene lactones film-forming resin described in 1 or 2, it is characterized in that: the compound primarily of following mass parts forms:
Containing sesquiterpene lactones film-forming resin 10 ~ 35 parts;
Photic sour 0.5 ~ 6 part;
Solvent 70 ~ 90 parts;
Organic bases 0.01 ~ 0.5 part;
Described photic acid be meet chemical general formula ( ) or ( ) one of sulfosalt, or meet chemical general formula ( ) one of diaryl group iodized salt;
);
In formula: R 16, R 17, R 18h independently of one another, carbonatoms be 1 ~ 20 alkyl or carbonatoms be the alkoxyl group of 1 ~ 20; Q=0 ~ 12;
);
In formula: R 19h, carbonatoms be 1 ~ 20 alkyl or carbonatoms be the alkoxyl group of 1 ~ 20; R=0 ~ 12;
);
In formula: R 20, R 21h independently of one another, carbonatoms be 1 ~ 20 alkyl or carbonatoms be the alkoxyl group of 1 ~ 20; S=0 ~ 12;
Described solvent is at least one in 1-Methoxy-2-propyl acetate, propylene glycol list Acetic Ester, dihydroxypropane single-ether, 1-Methoxy-2-propyl acetate, tirethylene glycol methyl ether, tirethylene glycol ether, N-BUTYL ACETATE, acetic acid peopentyl ester, ethyl lactate, methyl ethyl ketone and methyl iso-butyl ketone (MIBK);
Described organic bases is selected from least one in tripropyl amine, Tributylamine, tri-isobutylamine, trioctylamine, trolamine, triethoxy thanomin, trimethoxy methoxy ethyl amine and Tetramethylammonium hydroxide.
Technique scheme further illustrates as follows:
1. in such scheme, described in meet chemical general formula ( ) or ( ) sulfosalt be: triphenyl sulfosalt, three p-methylphenyl sulfosalts, the three pairs of tert-butyl-phenyl sulfosalts, three (3,5-3,5-dimethylphenyl) sulfosalt, three (3,5-di-tert-butyl-phenyl) sulfosalt, its coordination anion is: trifluoromethane sulfonic acid, perfluoro butyl sulfonic acid, p-methylphenyl sulfonic acid, naphthene sulfonic acid.
2. in such scheme, described in meet chemical general formula ( ) diaryl group iodized salt be: diphenyl iodnium, di-p-tolyl salt compounded of iodine, two pairs of tert-butyl-phenyl salt compounded of iodine, its coordination anion is: trifluoromethane sulfonic acid, perfluoro butyl sulfonic acid, p-methylphenyl sulfonic acid, naphthene sulfonic acid, camphorsulfonic acid.
Because technique scheme is used, the present invention compared with prior art has following advantages and effect:
1, the present invention is containing sesquiterpene lactones film-forming resin and positivity dry method exposure 193nm photoresist material thereof, the polymerisable monomer introduced in the photoresist material film-forming resin of current ArF (193nm) laser explosure containing natural product sesquiterpene lactones forms the brand-new film-forming resin of a class, this new film-forming resin can increase the adhesive property between photoresist material and silicon chip, due to the increase of the carbon atom density of film-forming resin, also by improving the resistance toheat of photoresist material, its anti-etching performance is greatly improved
2, utilize natural product as electronic product raw material, not only cost is low, environmental protection, and itself be polycyclic aliphatic alkane, its structure and adamantane are seemingly, also there is stereoisomerism and optical activity, imparting new development space for improving photoresist material performance, opening the gate that a fan is new.
3, the present invention is containing sesquiterpene lactones film-forming resin and positivity 193nm photoresist material thereof, due to sesquiterpene lactones alkene or sesquiterpene lactones alcohol molecular weight large, boiling point is very high, thus the problem of the exposure machine camera lens avoiding the hydrolysis of ester group when exposing and form gas overflowing (outing gas) and affect litho pattern and damage costliness occurs.
 
Specific embodiments
Below in conjunction with embodiment, the invention will be further described:
Embodiment one: a kind of multipolymer film-forming resin containing natural product sesquiterpene lactones, by copolymerized monomers and content thereof, under radical initiator existent condition, carry out copolyreaction by heating and be prepared from:
Methacrylic acid butyrolactone-2-ester 1.70 grams;
Methacrylic acid pentamethylene isobornyl thiocyanoacetate 2.20 grams;
Methacrylic acid short Docetaxel A ester 6.38 grams.
Preparation method is: be equipped with electric mixer at one, condenser, thermometer, temperature regulator, in the 100ml there-necked flask of heating jacket and nitrogen inlet, add methacrylic acid butyrolactone-2-ester (CAS# 195000-66-9) 1.70 grams, methacrylic acid pentamethylene isobornyl thiocyanoacetate (CAS# 34759-34-7) 2.20 grams, the short Docetaxel ester of methacrylic acid 6.38 grams, tetrahydrofuran (THF) 60 grams, under agitation logical nitrogen 10 minutes, then 60 ~ 70 DEG C are heated to, drip azo two isobutyl fine (AIBN) 0.56 gram in 20 minutes to make solution at 10 grams of tetrahydrofuran (THF)s and then add in reaction system, continue reaction backflow after 24 hours, then room temperature is cooled to.Extract three times with heptane, polymers soln precipitates in pure water, obtains polymer solids, yield 72% after vacuum-drying.
Embodiment two: a kind of multipolymer film-forming resin containing natural product sesquiterpene lactones, by copolymerized monomers and content thereof, under radical initiator existent condition, carry out copolyreaction by heating and be prepared from:
Methacrylic acid butyrolactone-2-ester 1.70 grams;
Isobornyl methacrylate 2.22 grams;
Methacrylic acid short Docetaxel A ester 6.38 grams.
Preparation method is: be equipped with electric mixer at one, condenser, thermometer, temperature regulator, in the 100ml there-necked flask of heating jacket and nitrogen inlet, add methacrylic acid butyrolactone-2-ester 1.70 grams, isobornyl methacrylate 2.22 grams, the short Docetaxel ester of methacrylic acid 6.38 grams, tetrahydrofuran (THF) 60 grams, under agitation logical nitrogen 10 minutes, then 65 ~ 70 DEG C are heated to, add azo two isobutyl fine (AIBN) 0.55 gram in 10 grams of tetrahydrofuran (THF)s, to make solution then add in reaction system, continue reaction backflow after 8 ~ 24 hours, then room temperature is cooled to.Extract three times with heptane, polymers soln precipitates in pure water, obtains polymer solids, yield 74% after vacuum-drying.
Embodiment three: a kind of multipolymer film-forming resin containing natural product sesquiterpene lactones, by copolymerized monomers and content thereof, under radical initiator existent condition, carry out copolyreaction by heating and be prepared from:
Methacrylic acid-1-ethyl cyclopentanol ester 3.64 grams;
Methacrylic acid short Docetaxel A ester 6.38 grams;
Preparation method is: be equipped with in the 100ml there-necked flask of electric mixer, condenser, thermometer, temperature regulator, heating jacket and nitrogen inlet at one, add methacrylic acid-1-ethyl cyclopentanol ester 3.64 grams, methacrylic acid short Docetaxel A ester 6.38 grams, tetrahydrofuran (THF) 60 grams, under agitation logical nitrogen 10 minutes, then 60 ~ 70 DEG C are heated to, add azo two isobutyl fine (AIBN) 0.55 gram in 10 grams of tetrahydrofuran (THF)s, to make solution then add in reaction system, continue reaction backflow after 18 hours, be then cooled to room temperature.Extract three times with heptane, polymers soln precipitates in pure water, obtains polymer solids, yield 75% after vacuum-drying.
Embodiment four: a kind of multipolymer film-forming resin containing natural product sesquiterpene, under radical initiator existent condition, carry out copolyreaction by copolymerized monomers and be prepared from:
Methacrylic acid-1-ethyl cyclopentanol ester 2.91 grams;
Norborneol lactone is to methacrylic ester 6.38 grams;
Lily magnolia lactone methacrylic ester 1.28 grams.
Preparation method is: be equipped with electric mixer at one, condenser, thermometer, temperature regulator, in the 100ml there-necked flask of heating jacket and nitrogen inlet, add methacrylic acid-1-ethyl cyclopentanol ester 2.91 grams, lily magnolia lactone methacrylic ester 1.28 grams, norborneol lactone is to methacrylic ester 6.38 grams, tetrahydrofuran (THF) 70 grams, under agitation logical nitrogen 10 minutes, then 70 DEG C are heated to, drip azo two isobutyl fine (AIBN) 0.56 gram in 20 minutes to make solution at 10 grams of tetrahydrofuran (THF)s and then add in reaction system, continue reaction backflow after 24 hours, then room temperature is cooled to.Extract three times with heptane, polymers soln precipitates in pure water, obtains polymer solids, yield 70% after vacuum-drying.
Embodiment five: a kind of multipolymer film-forming resin containing natural product sesquiterpene lactones, be polymerized in the presence of a free-radical initiator by comonomer, its equation is as follows:
Methacrylic acid-1-cyclohexyl alcohol ester 5.88 grams;
Lily magnolia lactone methacrylic ester 6.38 grams.
Preparation method is: be equipped with in the 100ml there-necked flask of electric mixer, condenser, thermometer, temperature regulator, heating jacket and nitrogen inlet at one, add methacrylic acid-1-cyclohexyl alcohol ester 5.88 grams, methacrylic acid short Docetaxel A ester 6.38 grams, tetrahydrofuran (THF) 60 grams, under agitation logical nitrogen 10 minutes, is then heated to 60 ~ 70 DEG C, adds azo two isobutyl fine (AIBN) 0.64 gram of solution in 10 grams of THF, continue reaction backflow after 8 ~ 24 hours, be then cooled to room temperature.Polymers soln precipitates in pure water, obtains polymer solids, yield 75% after vacuum-drying.
Embodiment six: a kind of multipolymer film-forming resin containing natural product sesquiterpene lactones, be polymerized in the presence of a free-radical initiator by comonomer, reaction equation is as follows:
Methacrylic acid-1-cyclohexyl alcohol ester 2.45 grams;
Methacrylic acid-3-hydroxyadamantane alcohol ester 5.90 grams;
Methacrylic acid lily magnolia lactone ester 1.33 grams.
Preparation method is: be equipped with in the 100ml there-necked flask of electric mixer, condenser, thermometer, temperature regulator, heating jacket and nitrogen inlet at one, add methacrylic acid-1-cyclohexyl alcohol ester 2.45 grams, methacrylic acid-3-hydroxyadamantane alcohol ester 5.90 grams, methacrylic acid lily magnolia lactone ester 1.33 grams, tetrahydrofuran (THF) 60 grams, under agitation logical nitrogen 10 minutes, then 60 ~ 70 DEG C are heated to, add azo two isobutyl fine (AIBN) 0.49 gram of solution in 10 grams of THF, continue reaction backflow after 24 hours, be then cooled to room temperature.Polymers soln precipitates in pure water, obtains polymer solids, yield 70% after vacuum-drying.
Embodiment seven: a kind of multipolymer film-forming resin containing natural product sesquiterpene lactones, be polymerized in the presence of a free-radical initiator by comonomer, reaction equation is as follows:
Methacrylic acid-2-methyl adamantane alcohol ester 6.90 grams;
Methacrylic acid butyrolactone-2-ester 4.08 grams;
Chloranthalactone alcohol methacrylic ester 1.91 grams.
Preparation method is: be equipped with in the 100ml there-necked flask of electric mixer, condenser, thermometer, temperature regulator, heating jacket and nitrogen inlet at one, add methacrylic acid butyrolactone-2-ester ester 4.08 grams, methacrylic acid-2-methyl adamantane alcohol ester 6.90 grams, chloranthalactone alcohol methacrylic ester 1.91 grams, tetrahydrofuran (THF) 70 grams, under agitation logical nitrogen 10 minutes, then 60 ~ 70 DEG C are heated to, add azo two isobutyl fine (AIBN) 0.64 gram of solution in 10 grams of THF, continue reaction backflow after 8 ~ 24 hours, be then cooled to room temperature.Polymers soln precipitates in pure water, obtains polymer solids, yield 67% after vacuum-drying.
Embodiment eight ~ embodiment 12, positivity dry method exposure 193nm photoresist material preparation containing the multipolymer film-forming resin of natural product sesquiterpene lactones:
(1) photic acid: embodiment eight: triphenyl trifluoromethyl sulfosalt, coordination anion is perfluoro butyl sulfonic acid; Embodiment nine: triphenyl sulfosalt, coordination anion is perfluoro butyl sulfonic acid; Embodiment ten: three p-methylphenyl sulfosalt, coordination anion is naphthene sulfonic acid; Embodiment 11: two pairs of tert-butyl-phenyl salt compounded of iodine, coordination anion is trifluoromethane sulfonic acid; Embodiment 12: three pairs of tert-butyl-phenyl sulfosalts, coordination anion is trifluoromethane sulfonic acid.
(2) solvent: embodiment eight: 1-Methoxy-2-propyl acetate; Embodiment nine: acetic acid peopentyl ester; Embodiment ten: methyl ethyl ketone; Embodiment 11: dihydroxypropane single-ether, 1-Methoxy-2-propyl acetate; Embodiment 12: N-BUTYL ACETATE, ethyl lactate.
(3) organic bases: embodiment eight: tri-isobutylamine; Embodiment nine: trimethoxy methoxy ethyl amine; Embodiment ten: trolamine; Embodiment 11: tri-isobutylamine; Embodiment 12: tripropyl amine.
(4) collocation method of the photoresist material of embodiment eight:
A kind of compound method of the deep ultraviolet positive photoresist containing natural product sesquiterpene: in clean 250 new ml polypropylene Plastic Bottles, add the multipolymer of preparation in 5.32 grams of embodiments one, 0.217 gram of triphenyl trifluoromethyl sulfosalt, 70.0 grams of electronic grade propylene glycol methyl ether acetate (PGMEA) solvents, and 0.2 gram of n-Butyl Amine 99,0.12 gram of tensio-active agent.This mixture is fixed on a mechnical oscillator, at room temperature shakes 10 ~ 24 hours, makes it fully dissolve.With the metre filter one time of 0.5 micron pore size, then use the metre filter one time of 0.05 micron pore size.
Lithography experiments method and result: the photoresist material of above-mentioned preparation is 12 " silicon chip rotates film forming with the speed of 2000 ~ 6000 revs/min, 120 DEG C of hot plates toasted for 90 seconds, then exposes with on 193nm step-by-step exposure machine.Exposure intensity 10-50 mJ/cm 2.On 110 DEG C of hot plates, toasted for 90 seconds after exposure, finally developed for 60 seconds in 2.38% TMAH developing solution (23 DEG C) again, after drying, uses submicroscopy lithographic results.Result proves that this photoresist material resolving power can reach 0.13 ~ 0.10 μm, and has good photoetching process operation allowed band.
(5) Formulation Summary of embodiment eight ~ embodiment 12 is as following table, and compound method is with embodiment eight, and film-forming resin adopts embodiment two ~ six successively.The resolving power of gained photoresist material, anti-etching performance and adhesion evaluation result are as shown in table 2 below:
Table 2
Note: during the assessment of (1) photoresist material, because processing requirement is different, resolving power is all good in 0.13um-0.10um scope;
(2) in dry etching assessment, under setting processing condition, Liu Mo Shuais≤80% be +++; Liu Mo Shuais≤60% be ++; Liu Mo Shuais≤40% for+; Liu Mo Shuais≤30% for defective;
(3) in adhesion evaluation, during microscopic examination development, photoetching offset plate figure, lines occur with or without flaw phenomenons such as being shifted, being out of shape or come off.Be qualified without any above-mentioned flaw, it is defective for finding that there is any above-mentioned flaw.
 
Above-described embodiment, only for technical conceive of the present invention and feature are described, its object is to person skilled in the art can be understood content of the present invention and implement according to this, can not limit the scope of the invention with this.All equivalences done according to spirit of the present invention change or modify, and all should be encompassed within protection scope of the present invention.

Claims (6)

1. one kind contains sesquiterpene lactones film-forming resin, it is characterized in that: described film-forming resin by comonomer under radical initiator existent condition, carry out copolyreaction in solvent to be prepared from, it is characterized in that: the molecular weight of described film-forming resin is 4,000 ~ 1,000,000, molecular weight distribution is 1.4 ~ 2.4; Described comonomer is mainly the compound of following masses percentage composition:
Containing the component units 10% ~ 60% of natural product sesquiterpene lactones,
Containing acid-labile group monomer 5% ~ 40%,
Other property regulation constituent monomers 1% ~ 20%;
The described component units containing natural product sesquiterpene lactones refer to meet chemical general formula ( ) (methyl) acrylic ester compound of at least one sesquiterpenoid;
(II);
Described containing acid-labile group monomer be meet chemical general formula ( ) formula and ( ) at least one compound:
);
Chemical general formula ( ) R in formula 2for H or CH 3;
Chemical general formula ( ) R in formula 3for can leavings group, can one of the optional substituents group of leavings group, as shown in (IV):
(IV);
Wherein Y=-CH 3or-CH 2cH 3.
2. according to claim 1 containing sesquiterpene lactones film-forming resin, it is characterized in that: described chemical general formula ( ) in R base be the sesquiterpene lactones alcohol shown in table 1, or be ethylenic corresponding to the sesquiterpene lactones alcohol shown in table 1, described sesquiterpene lactones alcohol is as shown in table 1 below:
3. according to claim 1 containing sesquiterpene lactones film-forming resin, it is characterized in that: described initiator is the radical initiator of azo initiator, superoxide; Described azo initiator is that azo two isobutyl is fine or azo two is fine for different heptan, and the radical initiator of described superoxide is tert-butyl hydroperoxide pivalate, tertbutyl peroxide, phenylformic acid hydrogen peroxide or benzoyl peroxide etc.; Described initiator amount is 0.3% ~ 15% of described comonomer gross weight.
4. application rights requires the positivity dry method exposure 193nm photoresist material made containing sesquiterpene lactones film-forming resin according to any one of 1 ~ 3, it is characterized in that: the compound primarily of following mass parts forms:
Containing sesquiterpene lactones film-forming resin 10 ~ 35 parts;
Photic sour 0.5 ~ 6 part;
Solvent 70 ~ 90 parts;
Organic bases 0.01 ~ 0.5 part;
Described photic acid be meet chemical general formula ( ) or ( ) one of sulfosalt, or meet chemical general formula ( ) one of diaryl group iodized salt;
);
In formula: R 16, R 17, R 18h independently of one another, carbonatoms be 1 ~ 20 alkyl or carbonatoms be the alkoxyl group of 1 ~ 20; Q=0 ~ 12;
);
In formula: R 19h, carbonatoms be 1 ~ 20 alkyl or carbonatoms be the alkoxyl group of 1 ~ 20; R=0 ~ 12;
);
In formula: R 20, R 21h independently of one another, carbonatoms be 1 ~ 20 alkyl or carbonatoms be the alkoxyl group of 1 ~ 20; S=0 ~ 12;
Described solvent is at least one in 1-Methoxy-2-propyl acetate, propylene glycol list Acetic Ester, dihydroxypropane single-ether, 1-Methoxy-2-propyl acetate, tirethylene glycol methyl ether, tirethylene glycol ether, N-BUTYL ACETATE, acetic acid peopentyl ester, ethyl lactate, methyl ethyl ketone and methyl iso-butyl ketone (MIBK);
Described organic bases is selected from least one in tripropyl amine, Tributylamine, tri-isobutylamine, trioctylamine, trolamine, triethoxy thanomin, trimethoxy methoxy ethyl amine and Tetramethylammonium hydroxide.
5. positivity dry method according to claim 4 exposure 193nm photoresist material, is characterized in that: described in meet chemical general formula ( ) or ( ) sulfosalt be: triphenyl sulfosalt, three p-methylphenyl sulfosalts, the three pairs of tert-butyl-phenyl sulfosalts, three (3,5-3,5-dimethylphenyl) sulfosalt, three (3,5-di-tert-butyl-phenyl) sulfosalt, its coordination anion is: trifluoromethane sulfonic acid, perfluoro butyl sulfonic acid, p-methylphenyl sulfonic acid, naphthene sulfonic acid.
6. positivity dry method according to claim 4 exposure 193nm photoresist material, is characterized in that: described in meet chemical general formula ( ) diaryl group iodized salt be: diphenyl iodnium, di-p-tolyl salt compounded of iodine, two pairs of tert-butyl-phenyl salt compounded of iodine, its coordination anion is: trifluoromethane sulfonic acid, perfluoro butyl sulfonic acid, p-methylphenyl sulfonic acid, naphthene sulfonic acid, camphorsulfonic acid.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108373520A (en) * 2017-12-22 2018-08-07 江苏汉拓光学材料有限公司 A kind of acrylate copolymer and the photoetching compositions comprising it
CN116987225A (en) * 2023-09-27 2023-11-03 甘肃华隆芯材料科技有限公司 Photoresist polymer for 193nm, preparation method thereof and photoresist composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09230597A (en) * 1996-02-21 1997-09-05 Yasuhara Chem Kk Positive type photoresist composition
CN1745114A (en) * 2003-01-31 2006-03-08 三菱丽阳株式会社 Resist polymer and resist composition
CN103387636A (en) * 2013-07-05 2013-11-13 昆山西迪光电材料有限公司 Sesquiterpene-containing film-forming resin and positive 248 nm photoresist thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09230597A (en) * 1996-02-21 1997-09-05 Yasuhara Chem Kk Positive type photoresist composition
CN1745114A (en) * 2003-01-31 2006-03-08 三菱丽阳株式会社 Resist polymer and resist composition
CN103387636A (en) * 2013-07-05 2013-11-13 昆山西迪光电材料有限公司 Sesquiterpene-containing film-forming resin and positive 248 nm photoresist thereof

Cited By (3)

* Cited by examiner, † Cited by third party
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CN108373520A (en) * 2017-12-22 2018-08-07 江苏汉拓光学材料有限公司 A kind of acrylate copolymer and the photoetching compositions comprising it
CN116987225A (en) * 2023-09-27 2023-11-03 甘肃华隆芯材料科技有限公司 Photoresist polymer for 193nm, preparation method thereof and photoresist composition
CN116987225B (en) * 2023-09-27 2023-12-22 甘肃华隆芯材料科技有限公司 Photoresist polymer for 193nm, preparation method thereof and photoresist composition

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