CN1808272B - Photosensitive polymers containing adamantylalkyl vinyl ether, and resist compositions including the same - Google Patents
Photosensitive polymers containing adamantylalkyl vinyl ether, and resist compositions including the same Download PDFInfo
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- CN1808272B CN1808272B CN2006100057556A CN200610005755A CN1808272B CN 1808272 B CN1808272 B CN 1808272B CN 2006100057556 A CN2006100057556 A CN 2006100057556A CN 200610005755 A CN200610005755 A CN 200610005755A CN 1808272 B CN1808272 B CN 1808272B
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- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C9/00—Attaching auxiliary optical parts
- G02C9/02—Attaching auxiliary optical parts by hinging
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- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C9/00—Attaching auxiliary optical parts
- G02C9/04—Attaching auxiliary optical parts by fitting over or clamping on
Abstract
A photosensitive polymer includes a copolymer containing adamantylalkyl vinyl ether, and a resist composition includes the photosensitive polymer. For example, the photosensitive polymer may include acopolymer having a formula: wherein x is an integer between 1 and 4 inclusive, R<subscript>1 </highlight>is a hydrogen atom or a methyl group, R<subscript>2 </highlight>is an acid-labile C<subscript>4 </highlight>to C<subscript>20 </highlight>hydrocarbon group, p/(p+q+r)=0.1 to 0.4, q/(p+q+r)=0.1 to 0.5, and r/(p+q+r)=0.1 to 0.4.
Description
The application be that June 19, application number in 2003 are 03149009.3 the applying date, name is called the dividing an application of patented claim of " contain the photopolymer of adamantyl alkyl vinyl ether and contain the Photoresisting agent composition of this polymkeric substance ".
The cross reference of related application
This be January 19 calendar year 2001 application the non-temporary patent application 09/764150 of US (application promptly ' 150) the part continuation and require its right of priority, be hereby incorporated by for this reason.In addition, require the right of priority of the korean patent application 2002-34998 right on June 21st, 2002, be hereby incorporated by for this reason.
' 150 applications are non-temporary patent applications 09/576053 of US of application on May 23rd, 2000, now are that the part of United States Patent (USP) 6517990 continues.In addition, 150 ' application requires the right of priority of the US temporary patent application 60/198761 of application on April 21st, 2000, require the right of priority of the korean patent application 00-2489 on January 19th, 2000, require the right of priority of the korean patent application 00-20603 on April 19th, 2000.
Invention field
The present invention relates to the Photoresisting agent composition of photopolymer and chemical amplifying type.More particularly, the present invention relates to comprise the photopolymer that contains adamantyl alkyl vinyl ether multipolymer, and contain the Photoresisting agent composition of this polymkeric substance.
Background technology
When semiconductor devices became more Highgrade integration, the photoetching method that uses in making such device must can form fine pattern.For example, the pattern of needs 0.2 μ m or smaller szie is used to have the semiconductor memory device above the 1G byte capacity.Therefore, the application of traditional photoresist material is restricted, and this is that the described wavelength of ultra-fine patterns is too big for forming because they are that the KrF excimer laser of 248nm is used with wavelength.Therefore having proposed a kind of new photoresist material uses with the ArF excimer laser.This is that its wavelength than KrF excimer laser is little because the wavelength of ArF excimer laser is 193nm.
Compare with traditional photoresist material, there are several shortcomings in the photoresist material that is designed for the use of ArF excimer laser at present.These problems of the most normal appearance are low penetrabilitys, and anti-dry ecthing is very poor.
Common use acryloyl-or (methyl) acryloyl group polymkeric substance, know as ArF photoresist material.The representative example of such polymkeric substance comprises the polymeric material of poly-(methacrylate) base.But the also possible shortcoming of such polymkeric substance, anti-dry ecthing is very poor.The selectivity of these materials is too low usually so that can not use plasma gas to carry out dry etch process.
Therefore, in the effort that strengthens anti-dry ecthing, will contain the alicyclic compound of strong anti-dry ecthing, for example isobornyl, adamantyl (adamantyl) or tristane base (decanyl) can be incorporated on the main polymer chain.But owing to have only the polymkeric substance of fraction to be occupied by alicyclic compound, anti-dry ecthing is still very weak.And, because alicyclic compound is hydrophobic,, stays in the polymkeric substance such alicyclic compound, to the poor adhesion of the primer of the photoresist layer that obtains by this polymkeric substance if being held.
As the traditional polymkeric substance of another kind, the alternating copolymer of cycloolefin-maleic anhydride (COMA) is proposed.Although for example the required relevant raw material production cost of COMA system is very cheap with producing multipolymer, the productive rate of polymkeric substance obviously descends.And for example the transmittance of 193nm polymkeric substance is very low in the shortwave district.In addition, because such polymkeric substance has alicyclic group on its main chain, it has very strong hydrophobicity, as a result the non-constant of their adhesion characteristic.
And because the architectural feature of its main chain, it is about 200 ℃ or higher that these polymkeric substance have very high glass transformation temperature.Therefore, be difficult to carry out annealing process to remove the free volume in the photoresist layer that obtains by these polymkeric substance.Therefore the photoresist layer is easily affected by environment.For example there is T-type top profile in the photoresist pattern.And to the delay (post-exposure delay) (PED) of developing, the photoresist layer demonstrates the stability decreases to ambiance after exposure, and this causes many problems having occurred in many processes of using the photoresist layer.
Summary of the invention
The invention provides such photopolymer, primer is had favourable cohesive, and have favourable anti-dry ecthing, described polymkeric substance can relatively inexpensively be produced.
The present invention also provides a kind of Photoresisting agent composition, and said composition is being used for example 193nm of shortwave district, and dark purple outskirt for example the exposure light source of 248nm carry out in the photoetching process, favourable lithographic plate (photoetching) performance can be provided.
According to an aspect of the present invention, provide and comprise photopolymer with general formula 1 multipolymer:
Wherein x is 1～4 integer, R
1Be hydrogen atom or methyl, R
2Be the unsettled C of acid
4～C
20Alkyl, p/ (p+q+r)=0.1～0.4, q/ (p+q+r)=0.1～0.5, and r/ (p+q+r)=0.1～0.4.The weight-average molecular weight of photopolymer is 3,000～50,000.
Preferably, R
2Be the tert-butyl group, THP trtrahydropyranyl or 1-ethoxyethyl group.R
2Be alicyclic hydrocarbon radical, example is 2-methyl-2-norborny (norbornyl), 2-ethyl-2-norborny, 2-methyl-2-isobornyl, 2-ethyl-2-isobornyl, 8-methyl-8-three rings [5,2,1,0
2,6] decyl, 8-ethyl-8-three rings [5,2,1,0
2,6] decyl, 2-methyl-2-adamantyl, 2-ethyl-2-adamantyl, 2-propyl group-2-adamantyl, 2-methyl-2-fenchyl or 2-ethyl-2-fenchyl.
According to an aspect of the present invention, provide and comprise photopolymer with general formula 2 multipolymers:
Wherein x is 1～4 integer, R
3Be hydrogen atom or hydroxyl, carboxyl, halogen, nitrile, alkyl, alkoxy, sulphonic acid ester, or be sour unsettled C
4～C
20Ester group, p/ (p+q+s)=0.1～0.4, q/ (p+q+s)=0.3～0.5, and s/ (p+q+s)=0.2～0.5.The weight-average molecular weight of photopolymer is 3,000～30,000.
Preferably, R
3Be the tert-butyl ester, tetrahydropyrans ester or 1-ethoxyethyl group ester group.And, R
3Be 2-methyl-2-norborneol ester, 2-ethyl-2-norborneol ester, 2-methyl-2-isobornyl thiocyanoacetate, 2-ethyl-2-isobornyl thiocyanoacetate, 8-methyl-8-three rings [5,2,1,0
2,6] last of the ten Heavenly stems ester, 8-ethyl-8-three rings [5,2,1,0
2,6] last of the ten Heavenly stems ester, 2-methyl-2-diamantane ester, 2-ethyl-2-diamantane ester, 2-propyl group-2-diamantane ester, 2-methyl-2-turnip ester or 2-ethyl-2-turnip ester group.
According to another aspect of the present invention, provide and comprise photopolymer with general formula 3 multipolymers:
Wherein x is 1～4 integer, R
1Be hydrogen atom or methyl, R
2Be C
4～C
20Alkyl, R
3Be hydrogen atom or hydroxyl, carboxyl, halogen, nitrile, alkyl, alkoxy, sulphonic acid ester, or be C
4～C
20Ester group, R
2And R
3At least one be acid-unstable group, p/ (p+q+r+s)=0.1～0.3, q/ (p+q+r+s)=0.2～0.5, r/ (p+q+r+s)=0.1～0.4, and s/ (p+q+r+s)=0.1～0.3.The weight-average molecular weight of photopolymer is 3,000～30,000.
According to another aspect of the present invention, provide Photoresisting agent composition, it comprises that photopolymer and light acid with general formula 1,2 or 3 produce thing (PAG).
Preferably, based on the general assembly (TW) of photopolymer, the PAG amount that comprises is about 1.0wt%～15wt%.Preferably, PAG comprises the potpourri of triarylsulfonium salt, diaryl group iodized salt, sulfonate or at least two kinds of such compounds.
According to the Photoresisting agent composition of one embodiment of the present invention, further comprise organic substrate.The content of organic substrate is about 0.01%～2.0wt% based on the amount of PAG.The example of organic substrate comprises the potpourri of triethylamine, triisobutyl amine, three iso-octyl amine, three isodecyl amine, triethanolamine and at least two kinds of such compounds.
The photopolymer of one embodiment of the present invention obtains by the co-polymer of adamantyl alkyl vinyl ether monomer and maleic anhydride, provides good cohesive to primer, and has high anti-dry ecthing.And the main chain of photopolymer has more flexible than traditional main chain, helps to reduce the glass transformation temperature of photopolymer.Therefore, Photoresisting agent composition therefrom has shown favourable lithographic plate (photoetching) performance when being used for photoetching process.
The description of invention preferred implementation
Describe nonrestrictive demonstration embodiment of the present invention in detail.
Embodiment 1
Synthetic 1-adamantyl ethyl vinyl ether
To be dissolved in the 100mL tetrahydrofuran, add the mercuric acetate of 5mol% subsequently in the ethyl vinyl ether adding round-bottomed flask of 36g (0.2mol) 1-diamantane ethanol and 72g (1.0mol).Afterwards, about 12 hours of reaction under refluxad.
After reaction was finished, the product that obtains was 50% monomer of wishing through vacuum distillation to obtain productive rate.
Embodiment 2
Synthetic 1-adamantyl ethylene methacrylic ether
The step identical with embodiment 1 carried out, and difference is to use 1-diamantane methyl alcohol to replace 1-diamantane ethanol, obtains productive rate and be the monomer of 40% hope.
Embodiment 3
Synthetic photopolymer
2.0g (10mmol) azoisobutyronitrile (AIBN) of maleic anhydride, 2.4g (10mmol) 2-methyl-2-adamantyl methacrylate and the 0.15g (3mol%) of the synthetic monomer of embodiment 1,1.0g (10mmol) is dissolved among the 10g THF, and uses nitrogen purging.Afterwards, with the product that obtains about 20 hours of about 65 ℃ of following polymerizations.
After polyreaction was finished, reaction product is slowly precipitation and filtration in excessive isopropyl alcohol (IPA).The precipitation of filtering is dissolved among an amount of TFH again, in normal hexane, precipitates again then.Dry about 24 hours of the filter thing that will obtain in remaining about 50 ℃ vacuum drying chamber is 70% to have the terpolymer of above-mentioned general formula to obtain productive rate.
The weight-average molecular weight (Mw) that obtains product is for about 9700, and polydispersity (Mw/Mn) is 1.7.
Embodiment 4
Synthetic photopolymer
2.0g (10mmol) azoisobutyronitrile (AIBN) of maleic anhydride, 2.2g (10mmol) 2-methyl-2 adamantyl acrylate and the 0.15g (3mol%) of the synthetic monomer of embodiment 1,1.0g (10mmol) is dissolved among the 10g THF, the mode identical with embodiment 3 carried out polymerization, obtains productive rate and is 68% and have the terpolymer of above-mentioned general formula.
The weight-average molecular weight (Mw) that obtains product is for about 10700, and polydispersity (Mw/Mn) is 1.9.
Embodiment 5
Synthetic photopolymer
2.0g (10mmol) azoisobutyronitrile (AIBN) of maleic anhydride, 2.0g (10mmol) 5-norborene-2-carboxylate and the 3mol% of the synthetic monomer of embodiment 1,2.0g (20mmol) is dissolved among the 12g THF, the mode identical with embodiment 3 carried out polymerization, obtains productive rate and is 55% and have the terpolymer of above-mentioned general formula.
The weight-average molecular weight (Mw) that obtains product is for about 8600, and polydispersity (Mw/Mn) is 1.9.
Embodiment 6
Synthetic photopolymer
2.0g (10mmol) azoisobutyronitrile (AIBN) of maleic anhydride, 0.5g (5mmol) norborene, 3.5g (15mmol) 2-methyl-2-adamantyl methacrylate and the 3mol% of the synthetic monomer of embodiment 1,1.5g (15mmol) is dissolved among the 15g THF, the mode identical with embodiment 3 carried out polymerization, obtains productive rate and is 70% and have the terpolymer of above-mentioned general formula.
The weight-average molecular weight (Mw) that obtains product is for about 9800, and polydispersity (Mw/Mn) is 1.8.
Embodiment 7
Preparation Photoresisting agent composition and flat board (photoetching) performance
The preparation method of the Photoresisting agent composition of embodiment of the present invention is described now.
At first, photopolymer that embodiment 3～6 is synthetic and light acid produce thing (PAG) and for example are dissolved in the various forms of solvents in Glycol Monomethyl ether acetic acid esters (PGMEA), ethyl lactate or the cyclohexanone, with preparation photoresist solution.If necessary, based on the amount of PAG, the addition that contains the organic substrate of amine is about 0.01～2.0wt%.And for regulating total dissolution velocity of photoresist, based on the amount of photopolymer, Photoresisting agent composition can further comprise the dissolution inhibitor of 5～25wt%.
Based on the amount of photopolymer, the amount of PAG is for being preferably about 1～15wt%.As PAG, can each independent or two or more inorganic salts or organic salt of being used in combination.The example of PAG comprises trifluoromethane sulfonic acid (triflate) triaryl matte, trifluoromethane sulfonic acid diaryl iodine, nine fluorine butyl sulfonic acid (nonaflate) triaryl mattes, nine fluorine butyl sulfonic acid diaryl iodine, succinimide (succinimidyl) trifluoromethane sulfonic acid (salt), 2,6-dinitro benzyl sulfonate etc.
For dull and stereotyped (photoetching) process, use the film filter of 0.2 μ m at first to filter twice of photoresistance agent solution to obtain Photoresisting agent composition.
The Photoresisting agent composition that obtains is handled through following process and is obtained pattern.
At first, preparation is the naked silicon chip or the silicon chip with bottom of patterning thereon, for example silicon oxide layer, silicon nitride layer or silicon oxynitride layer, and handle with hexamethyldisilazane (HMDS).Afterwards, to be applied to thickness with Photoresisting agent composition be about 0.3 μ m to form the photoresist layer to silicon chip.
Silicon chip with photoresist layer is to carry out about 60～90 seconds of prebake under 120 ℃～140 ℃ to desolvate to remove in temperature, uses multi-form exposure light source to carry out irradiation subsequently, for example dark UV (KrF or ArF), UV (EUV) far away and E-light beam or X-light.Next step for inducing chemical reaction at the exposed portion of photoresist layer, is to carry out post exposure bake (PEB) under 110 ℃～140 ℃ about 60～90 seconds in temperature.
Therefore, exposed portion has shown that for the very high dissolubility of developer solution described solution contains the Tetramethylammonium hydroxide (TMAH) of 2.38wt%.Therefore, during developing, exposed portion is dissolved well to be removed.Under the situation of using the ArF excimer laser, at about 8～about 25mJ/cm
2Exposure dose under can form the pattern of 120～140nm distance between centers of tracks.
The bottom that is patterned is silicon oxide film for example, by special etching gas for example plasma such as halogen or C
xF
yGas uses the photoresist pattern that obtains to carry out etching as mask.Subsequently, remove, form the silicon oxide pattern of wishing thus by ashing and the photoresist pattern that the wet process of using stripper will remain on the sheet.
Table 1 has been listed the evaluation result of dull and stereotyped lithography performance of the Photoresisting agent composition of embodiment of the present invention.
For the evaluation result of listing in the table 1, each photopolymer, trifluoromethane sulfonic acid triphenylsulfonium (TPS), nine fluorine butyl sulfonic acid triphenylsulfonium or its potpourri synthetic in embodiment 3～6 of 1g is as PAG, be dissolved in the 8g cyclohexane, 2mg joins wherein with dissolving fully as the three iso-octyl amine or the triisobutyl amine of organic substrate.Afterwards, use the film filter of 0.2 μ m to filter the photoresistance agent solution to obtain Photoresisting agent composition.
The Photoresisting agent composition that obtains is coated on thickness on silicon (Si) sheet of antireflection coating processing to about 0.3 μ m.
Afterwards, under the temperature and time condition that table 1 is listed, the sheet of coating through gently curing (SB), is used ArF excimer laser steeper (NA=0.6, σ=0.75) carries out irradiation, under the temperature and time condition that table 1 is listed, carry out post exposure bake (PEB) afterwards.Then, tetramethyl oxyammonia (TMAH) solution with 2.38wt% develops about 60 seconds to form the photoresist pattern.The resolution characteristics of photoresist pattern is shown in the table 1.
Reference table 1, in embodiment 7-1 three iso-octyl amine as organic substrate, and triisobutyl amine in embodiment 7-2～7-8 as organic substrate.
Table 1
| Embodiment | Polymkeric substance | PAG | SB | PEB | Dosage (mJ/cm 2) | Resolution (nm) |
| 7-1 | Embodiment 3 (1g) | TPS triflate(5mg) TPS nonaflate(10mg) | 120℃ /90sec | 120℃ /60sec | 15 | 140 |
| 7-2 | Embodiment 3 (1g) | TPS triflate(5mg) TPS nonaflate(10mg) | 120℃ /90sec | 120℃ /60sec | 17 | 120 |
| 7-3 | Embodiment 3 (1g) | TPS triflate(5mg) TPS nonaflate(10mg) | 120℃ /90sec | 130℃ /60sec | 16 | 120 |
| 7-4 | Embodiment 3 (1g) | TPS nonaflate(20mg) | 120℃ /90sec | 120℃ /90sec | 17 | 120 |
| 7-5 | Embodiment 3 (1g) | TPS triflate(5mg) TPS nonaflate(10mg) | 120℃ /90sec | 120℃ /90sec | 11 | 130 |
| 7-6 | Embodiment 4 (1g) | TPS triflate(5mg) TPS nonaflate(10mg) | 120℃ /90sec | 130℃ /90sec | 13 | 140 |
| 7-7 | Embodiment 5 (1g) | TPS nonaflate(15mg) | 120℃ /90sec | 130℃ /90sec | 18 | 140 |
| 7-8 | Embodiment 6 (1g) | TPS triflate(5mg) TPS nonaflate(10mg) | 120℃ /90sec | 120℃ /90sec | 16 | 120 |
As shown in table 1, in each embodiment, be 11～17mJ/cm at dosage
2Under can obtain 120～140nm distance between centers of tracks pattern clearly.
The photopolymer of embodiment of the present invention can by can with draw the electronics monomer, for example mother comes acid anhydrides, the vinethene compound that forms easily cross-linked copolymer in polymerization obtains.Particularly, photopolymer comprises the adamantyl alkyl vinyl ether as the main component of main chain.The adamantyl alkyl vinyl ether is to have C
1～C
4The compound of straight chain methylene.The Photoresisting agent composition that is obtained by photopolymer demonstrates than the improved anti-dry ecthing of traditional erosion resistant, and the cohesive good to primer can be provided.
Simultaneously, the alkyl chain that is included in the adamantyl alkyl vinyl ether in the photopolymer of the present invention can provide flexible to photopolymer.Therefore, the main chain of photopolymer has flexible, so these polymkeric substance have low relatively glass transformation temperature.Therefore, can realize that enough annealing effects are to remove the free volume of the photoresist layer that is obtained by photopolymer in the process of curing.Therefore the photoresist layer has the environment resistant of enhancing, even in the delay (PED) of after exposure, extremely developing.Therefore the Photoresisting agent composition of embodiment of the present invention demonstrates excellent dull and stereotyped lithography performance when being used for photoetching process, and it has advantage in next band semiconductor devices manufacturing.
Although with reference to preferred embodiment the present invention having been carried out concrete signal and description, but those of ordinary skill in the art should understand, under the prerequisite that does not deviate from the spirit and scope that limit as claims, the variation of various forms and details can be arranged wherein.
Claims (13)
1. one kind comprises the photopolymer with following general formula multipolymer:
Wherein x is 1～4 integer, R
3Be hydrogen atom or hydroxyl, carboxyl, halogen, nitrile, alkyl, alkoxy, sulphonic acid ester, or be sour unsettled C
4～C
20Ester group, p/ (p+q+s)=0.1～0.4, q/ (p+q+s)=0.3～0.5, and s/ (p+q+s)=0.2～0.5.
2. photopolymer as claimed in claim 1, wherein the weight-average molecular weight of polymkeric substance is 3,000～30,000.
3. photopolymer as claimed in claim 1, wherein R
3Be the tert-butyl ester, tetrahydropyrans ester or 1-ethoxyethyl group ester group.
4. photopolymer as claimed in claim 1, wherein R
3Be 2-methyl-2-norborneol ester, 2-ethyl-2-norborneol ester, 2-methyl-2-isobornyl thiocyanoacetate, 2-ethyl-2-isobornyl thiocyanoacetate, 8-methyl-8-three rings [5,2,1,0
2,6] last of the ten Heavenly stems ester, 8-ethyl-8-three rings [5,2,1,0
2,6] last of the ten Heavenly stems ester, 2-methyl-2-diamantane ester, 2-ethyl-2-diamantane ester, 2-propyl group-2-diamantane ester, 2-methyl-2-turnip ester or 2-ethyl-2-turnip ester group.
5. Photoresisting agent composition comprises:
(a) have the photopolymer of following general formula multipolymer:
Wherein x is 1～4 integer, R
3Be hydrogen atom or hydroxyl, carboxyl, halogen, nitrile, alkyl, alkoxy, sulphonic acid ester, or be sour unsettled C
4～C
20Ester group, p/ (p+q+s)=0.1～0.4, q/ (p+q+s)=0.3～0.5, and s/ (p+q+s)=0.2～0.5; And
(b) light acid produces thing.
6. Photoresisting agent composition as claimed in claim 5, wherein the weight-average molecular weight of polymkeric substance is 3,000～30,000.
7. Photoresisting agent composition as claimed in claim 5, wherein R
3Be the tert-butyl ester, tetrahydropyrans ester or 1-ethoxy ethyl ester base.
8. Photoresisting agent composition as claimed in claim 5, wherein R
3Be 2-methyl-2-norborneol ester, 2-ethyl-2-norborneol ester, 2-methyl-2-isobornyl thiocyanoacetate, 2-ethyl-2-isobornyl thiocyanoacetate, 8-methyl-8-three rings [5,2,1,0
2,6] last of the ten Heavenly stems ester, 8-ethyl-8-three rings [5,2,1,0
2,6] last of the ten Heavenly stems ester, 2-methyl-2-diamantane ester, 2-ethyl-2-diamantane ester, 2-propyl group-2-diamantane ester, 2-methyl-2-turnip ester or 2-ethyl-2-turnip ester group.
9. Photoresisting agent composition as claimed in claim 5, wherein based on the total amount of photosensitive polymerization, it is 1.0wt%～15wt% that biomass is produced in the light acid that comprises.
10. Photoresisting agent composition as claimed in claim 5, its photolytically acid produces the potpourri that thing comprises triarylsulfonium salt, diaryl group iodized salt, sulfonate or at least two kinds of such compounds.
11. Photoresisting agent composition as claimed in claim 5 further comprises organic substrate.
12. as the Photoresisting agent composition of claim 11, wherein the content of organic substrate is 0.01%～2.0wt% based on the sour amount that produces thing of light.
13. as the Photoresisting agent composition of claim 11, wherein organic substrate comprises the potpourri of triethylamine, triisobutyl amine, three iso-octyl amine, three isodecyl amine, triethanolamine and at least two kinds of such compounds.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2002-0034998A KR100510488B1 (en) | 2002-06-21 | 2002-06-21 | Photosensitive polymer including copolymer of adamantylalkyl vinyl ether and resist composition comprising the same |
| KR34998/2002 | 2002-06-21 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB031490093A Division CN1290881C (en) | 2002-06-21 | 2003-06-19 | Light sensitive polymer containing adamantane alkyl vinyl ether and optical retardent composition containing same |
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|---|---|
| CN1808272A CN1808272A (en) | 2006-07-26 |
| CN1808272B true CN1808272B (en) | 2010-06-16 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB031490093A Expired - Lifetime CN1290881C (en) | 2002-06-21 | 2003-06-19 | Light sensitive polymer containing adamantane alkyl vinyl ether and optical retardent composition containing same |
| CN2006100057556A Expired - Lifetime CN1808272B (en) | 2002-06-21 | 2003-06-19 | Photosensitive polymers containing adamantylalkyl vinyl ether, and resist compositions including the same |
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| JP (1) | JP4045210B2 (en) |
| KR (1) | KR100510488B1 (en) |
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| KR100689401B1 (en) * | 2004-07-30 | 2007-03-08 | 주식회사 하이닉스반도체 | Photoresist Polymer and Photoresist Composition Containing It |
| JP5345357B2 (en) * | 2008-08-29 | 2013-11-20 | 日本カーバイド工業株式会社 | 1,3-adamantane dimethanol monovinyl ether, 1,3-adamantane dimethanol divinyl ether and process for producing the same |
| KR101111491B1 (en) * | 2009-08-04 | 2012-03-14 | 금호석유화학 주식회사 | Novel copolymer and photoresist compositoin comprising the same |
| CN103073668B (en) * | 2013-01-09 | 2014-12-10 | 京东方科技集团股份有限公司 | Alkali soluble resin as well as preparation method, photosensitive resin composition and color filter |
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| CN1181520A (en) * | 1996-10-11 | 1998-05-13 | 三星电子株式会社 | Chemically amplified resist composition |
| CN1224728A (en) * | 1997-12-02 | 1999-08-04 | 三星电子株式会社 | Photosensitive polymer and chemically amplified resist composition using the same |
| US6306554B1 (en) * | 2000-05-09 | 2001-10-23 | Shipley Company, L.L.C. | Polymers containing oxygen and sulfur alicyclic units and photoresist compositions comprising same |
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|---|---|---|---|---|
| EP0999474B1 (en) * | 1998-05-25 | 2011-11-23 | Daicel Chemical Industries, Ltd. | Photoresist resin composition and method for forming a pattern |
| KR100604780B1 (en) * | 1999-07-23 | 2006-07-28 | 삼성전자주식회사 | Photosensitive polymer having alicyclic compound and acetal functional group in its backbone and photosensitive copolymer including the polymer |
| KR20010054675A (en) * | 1999-12-07 | 2001-07-02 | 윤종용 | Photosensitive polymer and chemical amplification type photoresist composition containing the same |
| KR20030000451A (en) * | 2001-06-25 | 2003-01-06 | 삼성전자 주식회사 | Photosensitive polymer and chemically amplified photoresist composition containing the same |
| KR100452415B1 (en) * | 2001-10-16 | 2004-10-12 | 주식회사 켐써치 | Photosensitive polymer for photoresist |
-
2002
- 2002-06-21 KR KR10-2002-0034998A patent/KR100510488B1/en active IP Right Grant
-
2003
- 2003-06-19 CN CNB031490093A patent/CN1290881C/en not_active Expired - Lifetime
- 2003-06-19 CN CN2006100057556A patent/CN1808272B/en not_active Expired - Lifetime
- 2003-06-20 JP JP2003176840A patent/JP4045210B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1181520A (en) * | 1996-10-11 | 1998-05-13 | 三星电子株式会社 | Chemically amplified resist composition |
| CN1224728A (en) * | 1997-12-02 | 1999-08-04 | 三星电子株式会社 | Photosensitive polymer and chemically amplified resist composition using the same |
| US6306554B1 (en) * | 2000-05-09 | 2001-10-23 | Shipley Company, L.L.C. | Polymers containing oxygen and sulfur alicyclic units and photoresist compositions comprising same |
Non-Patent Citations (1)
| Title |
|---|
| JP特开2000-72982A 2000.03.07 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004043807A (en) | 2004-02-12 |
| KR100510488B1 (en) | 2005-08-26 |
| KR20040000518A (en) | 2004-01-07 |
| CN1290881C (en) | 2006-12-20 |
| JP4045210B2 (en) | 2008-02-13 |
| CN1808272A (en) | 2006-07-26 |
| CN1472231A (en) | 2004-02-04 |
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