CN104387523B - Film-forming resin containing sesquiterpene lactoness and its positivity dry method exposure 193nm photoresists - Google Patents
Film-forming resin containing sesquiterpene lactoness and its positivity dry method exposure 193nm photoresists Download PDFInfo
- Publication number
- CN104387523B CN104387523B CN201410684392.8A CN201410684392A CN104387523B CN 104387523 B CN104387523 B CN 104387523B CN 201410684392 A CN201410684392 A CN 201410684392A CN 104387523 B CN104387523 B CN 104387523B
- Authority
- CN
- China
- Prior art keywords
- film
- forming resin
- lactoness
- general formula
- chemical general
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Abstract
The present invention discloses a kind of film-forming resin containing sesquiterpene lactoness and its positivity dry method exposure 193nm photoresists, its film-forming resin is carried out copolyreaction in a solvent and is prepared from by a kind of comonomer containing sesquiterpene lactoness is at least included under conditions of radical initiator presence;It is characterized in that:The molecular weight of the film-forming resin is 4,000~1,000,000, and molecular weight distribution is 1.4~2.4;The comonomer is mainly the compound of following masses percentage composition:Component units 10%~60% containing natural product sesquiterpene lactoness, monomer containing acid-labile group 5%~40%, other performance adjust constituent monomers 1% ~ 20%.Film-forming resin containing sesquiterpene lactoness disclosed by the invention and its positivity dry method exposure 193nm photoresists have good resolution, the adhesion property between photoresist and silicon chip can also be increased, improve the heat resistance of photoresist, improve its etch resistance energy, and be avoided that to form gas overflowing and affect litho pattern and damage the situation generation of expensive exposure machine camera lens.
Description
Technical field
The present invention relates to a kind of film-forming resin of lactone copolymers containing natural sesquiterpene and using the preparation of this film-forming resin
For with ArF laser(193nm)For the dry method exposure deep ultraviolet of exposure light source(DUV)Positivity chemical amplification type photoresist
Compositionss.
Background technology
Photoresist is to carry out the key function material of photoetching process in large scale integrated circuit industry.The nineties in last century opens
Beginning grow up with ArF laser(193nm)For the deep ultraviolet of exposure light source(DUV)Wave band exposure technology is widely used in system
Make in large scale integrated circuit, its resolution is up to 0.13~0.10 micrometer range.At present, as exposure sources are constantly updated,
Technological innovation and photoresist are updated, and resolution is improved constantly, can reach 0.065 micron.It is continuous due to resolution
The continuous improvement with photoetching process is improved, is also developed and perfect continuous as the photoresist of the functional material of figure transfer
In.There is following technical problem in actual process at present:(1)Photoresist is weak with the adhesiveness of base material silicon chip;(2)Photoresist
Thermostability and etch resistant poor performance;On the other hand, it is well known that China's natural product aboundresources, Oleum Terebinthinae, Colophonium, press leaf
The wide material sources such as alcohol, terpene and sesquiterpene and its lactone, yield are huge.Such as trees and many herbaceous plant such as pinaster, Cupressaceae, Eucalyptuss
In all contain the compounds such as high Oleum Terebinthinae, Colophonium, sesquiterpene and its lactone.
How national conditions are combined, by the compound from natural product, be applied to photoresist field in integrated circuit industry, and
Above-mentioned technical problem can be overcome while, solve existing photoresist to exposure machine camera lens harmful effect, become those skilled in the art
The direction of effort.
The content of the invention
First purpose of the present invention is to provide a kind of film-forming resin containing sesquiterpene lactoness, and this contains sesquiterpene lactoness film-forming resin
The adhesive property between photoresist film and silicon chip can be increased;Due to the increase of the carbon atom density of film-forming resin, will also improve
The heat resistance of photoresist, substantially improves its etch resistance energy, and forms gas overflowing when avoiding exposure and affect litho pattern
With the situation for damaging expensive exposure machine camera lens, further contrast and craft precision.
Second object of the present invention is to provide a kind of dry using positivity made by above-mentioned film-forming resin containing sesquiterpene lactoness
Method exposes 193nm photoresists.
To reach above-mentioned first goal of the invention, the technical solution used in the present invention is:A kind of film forming containing sesquiterpene lactoness
Resin, it is characterised in that:Film-forming resin carries out copolymerization by comonomer under conditions of radical initiator presence in a solvent
Reaction is prepared from;It is characterized in that:The molecular weight of the film-forming resin is 4,000~1,000,000, and molecular weight distribution is
1.4~2.4;The comonomer is mainly the compound of following masses percentage composition:
Component units 10%~60% containing natural product sesquiterpene;
Monomer containing acid-labile group 5%~40%;
Other performance adjusts constituent monomers 1% ~ 20%;
Above-mentioned technical proposal is described as follows:
1., in such scheme, the unit containing sesquiterpene lactoness is referred to and meets chemical general formula()At least one sesquialter
Terpene lactoness alcohol(Methyl)Acrylic ester compound;
(II);
The chemical general formula()The common sesquiterpene lactoness alcohol of middle R bases is as shown in table 1 below:
Table 1
The component units containing sesquiterpene lactoness typically by sesquiterpene lactoness alcohol with(Methyl)Acrylic acid(Or acryloyl chloride)
Esterification synthesis;Its ethylenic can first be converted into alcohol of formula and carry out above-mentioned esterification again.Such as:
The monomer containing acid-labile group is to meet chemical general formula()With()In at least one compound:
();
Chemical general formula()R in formula2For H or CH3;
Chemical general formula()R in formula3For can leaving group, can one of leaving group optional substituents group, such as(IV)
Shown in:
(IV);
Wherein Y=-CH3Or-CH2CH3。
2., in such scheme, the initiator is azo initiator, the radical initiator of peroxide;The azo
Initiator is that two isobutyl of azo is fine or azo is fine in two different heptan, and the radical initiator of the peroxide is that tert-butyl hydroperoxide is special
Valerate, tert-butyl hydroperoxide, benzoic acid hydrogen peroxide or benzoyl peroxide etc.;The initiator amount is described common
The 0.3%~15% of polycondensation monomer gross weight.
To reach above-mentioned second goal of the invention, the technical solution used in the present invention is:It is a kind of to apply 1 or 2 institute of claim
The positivity dry method exposure 193nm photoresists that the film-forming resin containing sesquiterpene lactoness stated is configured to, it is characterised in that:Mainly by following
The compound group of mass parts into:
10~35 parts of film-forming resin containing sesquiterpene lactoness;
Photic sour 0.5~6 part;
70~90 parts of solvent;
0.01~0.5 part of organic base;
The photic acid is to meet chemical general formula()Or()One of sulfosalt, or meet chemical general formula()One of diaryl group iodized salt;
();
In formula:R16、R17、R18H independently of one another, the alkyl that carbon number is 1~20 or carbon number be 1~20
Alkoxyl;Q=0~12;
();
In formula:R19H, the alkyl that carbon number is 1~20 or alkoxyl that carbon number is 1~20;R=0~
12,;
();
In formula:R20、R21H independently of one another, the alkyl that carbon number is 1~20 or alkane that carbon number is 1~20
Epoxide;S=0~12;
The solvent is propylene glycol methyl ether acetate, Propylene Glycol list Acetic Ester, dihydroxypropane single-ether, propylene glycol monomethyl ether acetic acid
Ester, tirethylene glycol methyl ether, tirethylene glycol ether, butyl acetate, acetic acid peopentyl ester, ethyl lactate, methyl ethyl ketone and first
At least one in base isobutyl ketone;
The organic base selected from tripropyl amine (TPA), tri-n-butylamine, triisobutylamine, trioctylamine, triethanolamine, triethoxy ethanolamine,
At least one in trimethoxy methoxy ethyl amine and Tetramethylammonium hydroxide.
Above-mentioned technical proposal is further described below:
1. it is in such scheme, described to meet chemical general formula()Or()Sulfosalt be:Triphenyl sulfosalt, three
P-methylphenyl sulfosalt, the three pairs of tert-butyl-phenyl sulfosalts, three(3,5- 3,5-dimethylphenyls)Sulfosalt, three(3,5- di-t-butyls
Phenyl)Sulfosalt, its coordination anion is:Trifluoromethane sulfonic acid, perfluoro butyl sulfonic acid, p-methylphenyl sulfonic acid, LOMAR PWA EINECS 246-676-2.
2. it is in such scheme, described to meet chemical general formula()Diaryl group iodized salt be:Diphenyl iodnium, two pairs
Tolyl iodine salt, two pairs of tert-butyl-phenyl iodine salt, its coordination anion is:It is trifluoromethane sulfonic acid, perfluoro butyl sulfonic acid, right
Toluenesulfonic acid, LOMAR PWA EINECS 246-676-2, camphorsulfonic acid.
As above-mentioned technical proposal is used, the present invention has following advantages and effect compared with prior art:
1st, film-forming resin containing sesquiterpene lactoness of the invention and its positivity dry method exposure 193nm photoresists, in current ArF
(193nm)The polymerisable monomer containing natural product sesquiterpene lactoness is introduced in the photoresist film-forming resin of laser explosure and forms one
The brand-new film-forming resin of class, this new film-forming resin can increase the adhesive property between photoresist and silicon chip, due to film forming
The increase of the carbon atom density of resin, also will improve the heat resistance of photoresist, substantially improves its etch resistance energy
2, by the use of natural product as electronic product raw material, not only low cost, environmental protection, and itself it is many ring greases
Fat alkane, its structure and adamantane seemingly, also with stereoisomerism and optical activity, be improve photoresist performance impart it is new
Development space, opens the new gate of a fan.
3rd, film-forming resin containing sesquiterpene lactoness of the invention and its positivity 193nm photoresist, due to sesquiterpene lactoness alkene or again
Sesquiterpene lactone alcohol molecular weight is big, and boiling point is very high, forms gas overflowing so as to avoid the hydrolysis of ester group in exposure(outing
gas)And affect litho pattern and damage the problem generation of expensive exposure machine camera lens.
Specific embodiment
With reference to embodiment, the invention will be further described:
Embodiment one:A kind of copolymer film-forming resin containing natural product sesquiterpene lactoness, by copolymerized monomers and its
Content, under conditions of radical initiator is present, carries out copolyreaction by heating and is prepared from:
1.70 grams of methacrylic acid butyrolactone -2- esters;
2.20 grams of methacrylic acid Pentamethylene. isobornyl thiocyanoacetate;
6.38 grams of the short Docetaxel A esters of methacrylic acid.
Preparation method is:At one equipped with motor stirrer, condenser, thermometer, temperature controller, heating mantle and nitrogen
In the 100ml there-necked flasks of gas entrance, methacrylic acid butyrolactone -2- esters are added(CAS# 195000-66-9)1.70 grams, methyl
2.20 grams of acrylic acid Pentamethylene. isobornyl thiocyanoacetate (CAS# 34759-34-7), 6.38 grams of the short Docetaxel ester of methacrylic acid, tetrahydrochysene
60 grams of furan, leads to nitrogen 10 minutes under agitation, is then heated to 60~70 DEG C, and in 20 minutes, two isobutyl of Deca azo is fine
(AIBN)Solution is made in 10 grams of tetrahydrofurans for 0.56 gram to be subsequently adding in reaction system, after continuing reaction backflow 24 hours, so
After be cooled to room temperature.With heptane extraction three times, polymer solution is precipitated in pure water, after vacuum drying polymer solids, receive
Rate 72%.
Embodiment two:A kind of copolymer film-forming resin containing natural product sesquiterpene lactoness, by copolymerized monomers and its
Content, under conditions of radical initiator is present, carries out copolyreaction by heating and is prepared from:
1.70 grams of methacrylic acid butyrolactone -2- esters;
2.22 grams of isobornyl methacrylate;
6.38 grams of the short Docetaxel A esters of methacrylic acid.
Preparation method is:At one equipped with motor stirrer, condenser, thermometer, temperature controller, heating mantle and nitrogen
In the 100ml there-necked flasks of gas entrance, 1.70 grams of methacrylic acid butyrolactone -2- esters, isobornyl methacrylate are added
2.22 grams, 6.38 grams of the short Docetaxel ester of methacrylic acid, 60 grams of tetrahydrofuran lead to nitrogen 10 minutes under agitation, are then heated to
65~70 DEG C, add two isobutyl of azo fine(AIBN)Solution is made in 10 grams of tetrahydrofurans for 0.55 gram and be subsequently adding reaction system
In, after continuing reaction backflow 8~24 hours, it is subsequently cooled to room temperature.With heptane extraction three times, polymer solution sinks in pure water
Form sediment, after vacuum drying, obtain polymer solids, yield 74%.
Embodiment three:A kind of copolymer film-forming resin containing natural product sesquiterpene lactoness, by copolymerized monomers and its
Content, under conditions of radical initiator is present, carries out copolyreaction by heating and is prepared from:
3.64 grams of methacrylic acid -1- ethyl cyclopentanol ester;
6.38 grams of the short Docetaxel A esters of methacrylic acid;
Preparation method is:At one equipped with motor stirrer, condenser, thermometer, temperature controller, heating mantle and nitrogen
In the 100ml there-necked flasks of gas entrance, 3.64 grams of methacrylic acid -1- ethyl cyclopentanol ester, the short Docetaxel A of methacrylic acid are added
6.38 grams of ester, 60 grams of tetrahydrofuran lead to nitrogen 10 minutes under agitation, are then heated to 60~70 DEG C, add two isobutyl of azo
It is fine(AIBN)Solution is made in 10 grams of tetrahydrofurans for 0.55 gram to be subsequently adding in reaction system, continue reaction backflow 18 hours
Afterwards, it is subsequently cooled to room temperature.With heptane extraction three times, polymer solution is precipitated in pure water, after vacuum drying polymer is solid
Body, yield 75%.
Example IV:A kind of copolymer film-forming resin containing natural product sesquiterpene, by copolymerized monomers in free radical
Initiator carries out copolyreaction under conditions of existing and is prepared from:
2.91 grams of methacrylic acid -1- ethyl cyclopentanol ester;
Norborneol lactone is to 6.38 grams of methacrylate;
1.28 grams of Drymotaenium miyoshianum (Mak.) Mak. lactone methacrylate.
Preparation method is:At one equipped with motor stirrer, condenser, thermometer, temperature controller, heating mantle and nitrogen
In the 100ml there-necked flasks of gas entrance, 2.91 grams of methacrylic acid -1- ethyl cyclopentanol ester, Drymotaenium miyoshianum (Mak.) Mak. lactone methacrylic acid are added
1.28 grams of ester, norborneol lactone lead to nitrogen 10 minutes, so under agitation to 6.38 grams of methacrylate, 70 grams of tetrahydrofuran
Post-heating to 70 DEG C, the fine (AIBN of two isobutyl of Deca azo in 20 minutes)Then 0.56 gram made solution in 10 grams of tetrahydrofurans
In adding reaction system, after continuing reaction backflow 24 hours, room temperature is subsequently cooled to.With heptane extraction three times, polymer solution
Precipitate in pure water, after vacuum drying, obtain polymer solids, yield 70%.
Embodiment five:A kind of copolymer film-forming resin containing natural product sesquiterpene lactoness, by comonomer in free radical
It is polymerized in the presence of initiator, its equation is as follows:
5.88 grams of methacrylic acid -1- cyclohexyls alcohol ester;
6.38 grams of Drymotaenium miyoshianum (Mak.) Mak. lactone methacrylate.
Preparation method is:At one equipped with motor stirrer, condenser, thermometer, temperature controller, heating mantle and nitrogen
In the 100ml there-necked flasks of gas entrance, 5.88 grams of methacrylic acid -1- cyclohexyls alcohol ester, the short Docetaxel A esters of methacrylic acid are added
6.38 grams, 60 grams of tetrahydrofuran leads to nitrogen 10 minutes under agitation, is then heated to 60 ~ 70 DEG C, adds two isobutyl of azo fine
(AIBN)0.64 gram of solution in 10 grams of THF, after continuing reaction backflow 8~24 hours, is subsequently cooled to room temperature.Polymer is molten
Liquid is precipitated in pure water, and polymer solids, yield 75% are obtained after vacuum drying.
Embodiment six:A kind of copolymer film-forming resin containing natural product sesquiterpene lactoness, by comonomer in free radical
It is polymerized in the presence of initiator, reaction equation is as follows:
2.45 grams of methacrylic acid -1- cyclohexyls alcohol ester;
5.90 grams of methacrylic acid -3- hydroxyadamantane alcohol ester;
1.33 grams of methacrylic acid Drymotaenium miyoshianum (Mak.) Mak. lactone ester.
Preparation method is:At one equipped with motor stirrer, condenser, thermometer, temperature controller, heating mantle and nitrogen
In the 100ml there-necked flasks of gas entrance, 2.45 grams of methacrylic acid -1- cyclohexyls alcohol ester, methacrylic acid -3- hydroxyls gold are added
Just 5.90 grams of alkanol ester, 1.33 grams of methacrylic acid Drymotaenium miyoshianum (Mak.) Mak. lactone ester, 60 grams of tetrahydrofuran, lead to nitrogen 10 minutes under agitation,
60 ~ 70 DEG C are then heated to, add two isobutyl of azo fine(AIBN)0.49 gram of solution in 10 grams of THF, continues reaction backflow
After 24 hours, room temperature is subsequently cooled to.Polymer solution is precipitated in pure water, and polymer solids, yield are obtained after vacuum drying
70%。
Embodiment seven:A kind of copolymer film-forming resin containing natural product sesquiterpene lactoness, by comonomer in free radical
It is polymerized in the presence of initiator, reaction equation is as follows:
6.90 grams of methacrylic acid -2- methyl adamantanes alcohol ester;
4.08 grams of methacrylic acid butyrolactone -2- esters;
1.91 grams of chloranthalactone alcohol methacrylate.
Preparation method is:At one equipped with motor stirrer, condenser, thermometer, temperature controller, heating mantle and nitrogen
In the 100ml there-necked flasks of gas entrance, 4.08 grams of methacrylic acid butyrolactone -2- esters ester, methacrylic acid -2- methyl Buddha's warrior attendants are added
6.90 grams of alkanol ester, 1.91 grams of chloranthalactone alcohol methacrylate, 70 grams of tetrahydrofuran lead to 10 points of nitrogen under agitation
Clock, is then heated to 60 ~ 70 DEG C, adds two isobutyl of azo fine(AIBN)0.64 gram of solution in 10 grams of THF, continuation react back
Stream was subsequently cooled to room temperature after 8~24 hours.Polymer solution is precipitated in pure water, obtains polymer solids, receive after vacuum drying
Rate 67%.
Eight~embodiment of embodiment 12, the positivity dry method of the copolymer film-forming resin containing natural product sesquiterpene lactoness expose
Light 193nm photoresists are prepared:
(1)Photic acid:Embodiment eight:Triphenyl trifluoromethyl sulfosalt, coordination anion are perfluoro butyl sulfonic acid;Implement
Example nine:Triphenyl sulfosalt, coordination anion are perfluoro butyl sulfonic acid;Embodiment ten:Three p-methylphenyl sulfosalts, coordination it is cloudy from
Son is LOMAR PWA EINECS 246-676-2;Embodiment 11:Two pairs of tert-butyl-phenyl iodine salt, coordination anion is trifluoromethane sulfonic acid;Embodiment ten
Two:Three pairs of tert-butyl-phenyl sulfosalts, coordination anion is trifluoromethane sulfonic acid.
(2)Solvent:Embodiment eight:Propylene glycol methyl ether acetate;Embodiment nine:Acetic acid peopentyl ester;Embodiment ten:Methyl second
Base ketone;Embodiment 11:Dihydroxypropane single-ether, propylene glycol methyl ether acetate;Embodiment 12:Butyl acetate, ethyl lactate.
(3)Organic base:Embodiment eight:Triisobutylamine;Embodiment nine:Trimethoxy methoxy ethyl amine;Embodiment ten:Three
Ethanolamine;Embodiment 11:Triisobutylamine;Embodiment 12:Tripropyl amine (TPA).
(4)The collocation method of the photoresist of embodiment eight:
A kind of compound method of the deep ultraviolet positive photoresist containing natural product sesquiterpene:Clean new 250
In milliliter Polypropylene bottle, the copolymer prepared in adding 5.32 grams of embodiments one, 0.217 gram of triphenyl trifluoromethyl sulfur
Salt, 70.0 grams of electronic grade propylene glycol methyl ether acetates(PGMEA)Solvent, and 0.2 gram of n-butylamine, 0.12 gram of surface activity
Agent.This mixture is fixed on a mechnical oscillator, is shaken 10~24 hours at room temperature so as to fully dissolved.It is micro- with 0.5
The filter in metre hole footpath is filtered one time, is then filtered one time with the filter of 0.05 micron pore size.
Lithography experiments method and result:The photoresist of above-mentioned preparation is 12 " on silicon chip with 2000~6000 revs/min
Speed rotates film forming, toasts 90 seconds, then exposed with 193nm step-by-step exposure machines on 120 DEG C of hot plates.Exposure intensity 10-
50 mJ/cm2.Toast 90 seconds on 110 DEG C of hot plates after exposure, finally again in 2.38% TMAH developer solutions(23℃)Middle development
60 seconds, after drying, use electron micrograph lithographic results.As a result this photoresist resolution is proved up to 0.13~0.10 μm,
And with good photoetching process operation allowed band.
(5)The Formulation Summary of eight~embodiment of embodiment 12 such as following table, compound method with embodiment eight, film-forming resin according to
Secondary employing embodiment two~six.The gained resolution of photoresist, etch resistance energy and adhesion evaluation result are as shown in table 2 below:
Table 2
Note:(1)When photoresist is assessed, as technological requirement is different, resolution is all in the range of 0.13um -0.10um
Well;
(2)In dry etching assessment, under setting process conditions, Liu Mo Shuai≤80% is +++;Liu Mo Shuai≤60% is
++;Liu Mo Shuai≤40% for+;Liu Mo Shuai≤30% is unqualified;
(3)In adhesion evaluation, when micro- sem observation develops, photoetching offset plate figure, lines whether there is displacement, deform or come off
Occur Deng flaw phenomenon.It is qualified without any of above flaw, it is unqualified that discovery has any of above flaw.
Above-described embodiment technology design only to illustrate the invention and feature, its object is to allow person skilled in the art
Scholar will appreciate that present disclosure and implement according to this, can not be limited the scope of the invention with this.It is all according to the present invention
Equivalence changes or modification that spirit is made, should all be included within the scope of the present invention.
Claims (5)
1. a kind of film-forming resin containing sesquiterpene lactoness, it is characterised in that:The film-forming resin is caused in free radical by comonomer
Under conditions of agent is present, copolyreaction is carried out in solvent and is prepared from, it is characterised in that:The molecular weight of the film-forming resin is 4,
000~1,000,000, molecular weight distribution is 1.4~2.4;The comonomer is mainly the chemical combination of following masses percentage composition
Thing:
Component units 10%~60% containing natural product sesquiterpene lactoness,
Monomer containing acid-labile group 5%~40%,
Other performance adjusts constituent monomers 1% ~ 20%;
The component units containing natural product sesquiterpene lactoness are referred to and meet chemical general formula()At least one sesquiterpenoid
's(Methyl)Acrylic ester compound;
(II);
The monomer containing acid-labile group is to meet chemical general formula()Formula and()In at least one compound:
();
Chemical general formula()R in formula2For H or CH3;
Chemical general formula()R in formula3For can leaving group, can one of leaving group optional substituents group, such as(IV)Middle institute
Show:
(IV);
Wherein Y=-CH3Or-CH2CH3;The chemical general formula()Middle R bases stem from the sesquiterpene lactoness alcohol shown in table 1, described
Sesquiterpene lactoness alcohol is as shown in table 1 below:
。
2. film-forming resin containing sesquiterpene lactoness according to claim 1, it is characterised in that:The initiator causes for azo
Agent, the radical initiator of peroxide;The azo initiator is azodiisobutyronitrile or 2,2'-Azobis(2,4-dimethylvaleronitrile), the peroxide
The radical initiator of compound is tert-butyl hydroperoxide pivalate, tert-butyl hydroperoxide, benzoic acid hydrogen peroxide or mistake
BP;The initiator amount is the 0.3%~15% of the comonomer gross weight.
3. positivity dry method exposure made by a kind of film-forming resin containing sesquiterpene lactoness using any one of claim 1 ~ 2
193nm photoresists, it is characterised in that:The main compound group by following mass parts into:
10~35 parts of film-forming resin containing sesquiterpene lactoness;
Photic sour 0.5~6 part;
70~90 parts of solvent;
0.01~0.5 part of organic base;
The photic acid is to meet chemical general formula()Or()One of sulfosalt, or meet chemical general formula()Two
One of aryl salt;
();
In formula:R16、R17、R18H independently of one another, the alkyl that carbon number is 1~20 or alkane that carbon number is 1~20
Epoxide;Q=0~12;
();
In formula:R19H, the alkyl that carbon number is 1~20 or alkoxyl that carbon number is 1~20;R=0~12,;
();
In formula:R20、R21H independently of one another, the alkyl that carbon number is 1~20 or alkoxyl that carbon number is 1~20;
S=0~12;
The solvent be Propylene Glycol list Acetic Ester, dihydroxypropane single-ether, propylene glycol methyl ether acetate, tirethylene glycol methyl ether, two
In condensed ethandiol ether, butyl acetate, acetic acid peopentyl ester, ethyl lactate, methyl ethyl ketone and methyl iso-butyl ketone (MIBK) at least one
Kind;
The organic base is selected from tripropyl amine (TPA), tri-n-butylamine, triisobutylamine, trioctylamine, triethanolamine, triethoxy ethanolamine, front three
At least one in Oxymethoxy ethylamine and Tetramethylammonium hydroxide.
4. positivity dry method according to claim 3 exposes 193nm photoresists, it is characterised in that:It is described to meet chemical general formula()Or()Sulfosalt be:Triphenyl sulfosalt, three p-methylphenyl sulfosalts, three pairs of tert-butyl-phenyl sulfosalts, which is matched somebody with somebody
Complex anion is:Trifluoromethane sulfonic acid, perfluoro butyl sulfonic acid.
5. positivity dry method according to claim 4 exposes 193nm photoresists, it is characterised in that:It is described to meet chemical general formula()Diaryl group iodized salt be:Diphenyl iodnium, di-p-tolyl iodine salt, two pairs of tert-butyl-phenyl iodine salt, its coordination
Anion is:Trifluoromethane sulfonic acid, perfluoro butyl sulfonic acid.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410684392.8A CN104387523B (en) | 2014-11-25 | 2014-11-25 | Film-forming resin containing sesquiterpene lactoness and its positivity dry method exposure 193nm photoresists |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410684392.8A CN104387523B (en) | 2014-11-25 | 2014-11-25 | Film-forming resin containing sesquiterpene lactoness and its positivity dry method exposure 193nm photoresists |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104387523A CN104387523A (en) | 2015-03-04 |
CN104387523B true CN104387523B (en) | 2017-03-29 |
Family
ID=52605494
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410684392.8A Active CN104387523B (en) | 2014-11-25 | 2014-11-25 | Film-forming resin containing sesquiterpene lactoness and its positivity dry method exposure 193nm photoresists |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104387523B (en) |
Families Citing this family (2)
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 |
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 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09230597A (en) * | 1996-02-21 | 1997-09-05 | Yasuhara Chem Kk | Positive type photoresist composition |
CN100406481C (en) * | 2003-01-31 | 2008-07-30 | 三菱丽阳株式会社 | Resist polymer and resist composition |
CN103387636B (en) * | 2013-07-05 | 2015-08-12 | 昆山西迪光电材料有限公司 | Containing film-forming resin and the positivity 248nm photoresist material thereof of sesquiterpene |
-
2014
- 2014-11-25 CN CN201410684392.8A patent/CN104387523B/en active Active
Also Published As
Publication number | Publication date |
---|---|
CN104387523A (en) | 2015-03-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104448113B (en) | Film-forming resin and its positivity immersion exposure 193nm photoresists containing sequiterpene | |
KR101569955B1 (en) | Curable copolymer and curable resin composition | |
TWI245972B (en) | Polymer for chemically amplified resist and chemically amplified resist composition containing the same | |
CN1976913B (en) | Lactone compounds, lactone-containing monomers, their polymers, resist compositions using same, and processes for forming patterns using same | |
JPH07252324A (en) | Vinyl monomer, its polymer and photosensitive resin composition made by using this polymer | |
CN103387636B (en) | Containing film-forming resin and the positivity 248nm photoresist material thereof of sesquiterpene | |
JP3236073B2 (en) | Resist composition and pattern forming method using the same | |
TW201314368A (en) | Chemically amplified positive resist composition for ArF immersion lithography and pattern forming process | |
JP2007299002A (en) | Photoresist composition and preparation method thereof | |
WO2008013207A1 (en) | Curable resin composition and method for forming cured coating film | |
CN102731715B (en) | Copolymer for resist comprising novel acryl based monomer and resin composition for resist comprising the same | |
TW200421036A (en) | Polymer for resist and resist composition | |
JP2005232095A (en) | Fluorine-containing cyclic compound, fluorine-containing polymer compound and resist material and pattern-forming method using the same | |
JP2008045125A (en) | Photosensitive polymer for extreme ultraviolet ray and deep ultraviolet ray and photoresist composition containing the same | |
JP4291905B2 (en) | Photosensitive polymer and chemically amplified resist composition using the same | |
JP4977347B2 (en) | Photoresist monomer and polymer having spiro cyclic ketal group, and photoresist composition containing the same | |
JP3642316B2 (en) | Chemically amplified resist monomer, chemically amplified resist polymer, chemically amplified resist composition, pattern formation method | |
JP2616250B2 (en) | Bridged cyclic hydrocarbon alcohols and intermediate compounds for photosensitive materials | |
CN100590529C (en) | Silicon containing 193nm negative photo resist and membrane forming resin | |
CN104387523B (en) | Film-forming resin containing sesquiterpene lactoness and its positivity dry method exposure 193nm photoresists | |
CN104403048B (en) | Film-forming resin and its positivity immersion exposure 193nm photoresists containing sesquiterpene lactone | |
CN101974119B (en) | Nano silicon containing deep ultraviolet positive photoresist and forming resin thereof | |
JPWO2019171957A1 (en) | New bifunctional (meth) acrylate compounds and polymers | |
CN108373520A (en) | A kind of acrylate copolymer and the photoetching compositions comprising it | |
TW200537244A (en) | Cyanoadamantyl compounds and polymers |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |