CN101042533B - Organosilane hardmask compositions and methods of producing semiconductor devices using the same - Google Patents
Organosilane hardmask compositions and methods of producing semiconductor devices using the same Download PDFInfo
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- CN101042533B CN101042533B CN2007100075135A CN200710007513A CN101042533B CN 101042533 B CN101042533 B CN 101042533B CN 2007100075135 A CN2007100075135 A CN 2007100075135A CN 200710007513 A CN200710007513 A CN 200710007513A CN 101042533 B CN101042533 B CN 101042533B
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
Abstract
The invention provides a hard mask combination, which is a organosilane polymer made by the reaction of one or more compounds; wherein, a R1, a R2 and a R3 can respectively be an alkyl, an acetoxy oran oxime, and a R4 can be a hydrogen, an alkyl, an aryl or an aralkyl; wherein, the organosilane polymer has a polydispersity of about 1.1 to 2. Si(OR<SUB>1</SUB>)(OR<SUB>2</SUB>)(OR<SUB>3</SUB>)R<SUB>4</SUB> (I).
Description
The application requires the right of priority of Korean application 2006-26211 that submitted on March 22nd, 2006 and the Korean application 2006-49341 that submitted on June 1st, 2006, and above-mentioned full content is incorporated herein by reference in the lump at this.
Technical field
The present invention relates to hard mask compositions, particularly relate to the organosilane hard mask compositions that is used for the resist underlying membrane.The invention still further relates to and adopt the organosilane hard mask compositions to make the method for semiconductor devices.
Background technology
In photoetching process,, antireflecting coating (ARC) material can be used for minimize such as the imaging layer of photoresists layer and the reflectivity between the substrate in order to obtain better resolution., because resist layer has the composition similar to the ARC material usually, therefore, with respect to imaging layer, this ARC material can provide very poor etching selectivity.Therefore, owing to when forming figure after etching ARC material, can remove most of imaging layer, therefore in etching step subsequently, can require to form additional patterns.
, in some optical patterning methods, anticorrosive additive material can not provide enough elching resistants, is delivered to layer below the anticorrosive additive material effectively with the figure with needs.In the application of reality, the so-called hard mask that is used for the resist lower membrane can be as the middle layer between the substrate of the resist of patterning and desirable patternization.For example, when use the ultrathin membrane anticorrosive additive material, want etched substrate very thick, when needing basic etch depth and/or needing to use special etchant to be used for particular substrate, just need be used for the hard mask of resist lower floor.The hard mask that is used for the resist lower membrane can be accepted figure from the resist layer of patterning, and this figure is passed to substrate.The hard mask that is used for the resist lower membrane should be able to stand figure need be passed to the etching process of following material.
For example, when processing such as the substrate of silicon, can be with the resist figure as mask.At this moment, resist can be had the thickness of reduction by miniature imageization.Therefore, because the mask character deficiency of resist, so the trade union that adds of substrate produces damage to substrate.Therefore, the lower membrane that can adopt a kind of method that resist pattern is at first passed to be used to process substrate (for example hard mask) is then used lower membrane to do as mask and is carved substrate.The lower membrane that is used to process substrate refers to the film that can form and can play the anti-reflecting layer effect below anti-reflective film.In this process, the rate of etch of resist can be close with the rate of etch of the lower membrane that is used to process substrate.Therefore, may need to form hard mask, be used to process the lower membrane between resist and the lower membrane, described hard mask also can be antireflecting.As a result, can in substrate, form by the lower membrane that is used to process substrate, be used to process the hard mask of lower membrane and the multilayer film that resist is formed.
Investigated multiple hard mask material.For example Japanese unexamined publication No.2000-0077018 has described at resist lower membrane formula of R
aSi (OR)
4-aThe purposes of polycondensation products of silane compound.A problem relevant with using this polycondensation products is that unreacted raw material and/or the low-molecular-weight secondary product that obtains can produce bad influence and cause the graphics performance variation the resist layer on the hard mask layer when polycondensation.
Therefore, wish identification hard mask compositions and use said composition to make unreacted raw material or the minimized method of low-molecular-weight secondary product in the hard mask layer of formation.
Summary of the invention
According to certain embodiments of the present invention, hard mask compositions can comprise the prepared organosilane polymer of reaction by one or more formulas I compound,
Si(OR
1)(OR
2)(OR
3)R
4 (I)
Wherein, R
1, R
2And R
3Can be alkyl, acetoxyl group or oxime independently of one another; And R
4Can be hydrogen, alkyl, aryl or aralkyl; And
Wherein organosilane polymer can have about 1.1 to about 2 polydispersity.
According to certain embodiments of the present invention, the reaction of one or more formulas (I) compound can be carried out in the presence of acidic catalyst, described acidic catalyst for example is nitric acid, sulfuric acid, a hydration p-toluenesulfonic acid, dithyl sulfate, 2,4,4,6-tetrabromo cyclohexyl dienone, benzoin tosylate (benzointosylate), 2-nitrobenzyl tosylate and organic sulfonic acid Arrcostab.
In addition, according to certain embodiments of the present invention, the described organosilane polymer of the prepared in reaction by one or more formulas (I) compound can have the structure of formula (II):
Wherein, R
4', R
4", R
4" ' and R
4" " can be hydrogen, alkyl, aryl or aralkyl independently of one another; And wherein organosilane polymer can have about 1.1 to about 2 polydispersity.
In addition, according to certain embodiments of the present invention, the method that forms semiconductor devices comprises
In substrate, form material layer;
On this material layer, form organic hard mask layer;
On this organic hard mask layer, form the antireflection hard mask layer by according to the embodiment of the present invention antireflective hardmask composition;
On this antireflection hard mask layer, form the photosensitive imaging layer;
Mode (patternwise) with figure is exposed to imaging layer under the radiation, to form the figure in radiant exposure zone in this imaging layer;
Optionally remove this imaging layer of part, this antireflection hard mask layer and this organic hard mask layer, to expose the part material layer; And
This material layer expose portion of etching is to form patterned material layer.
According to certain embodiments of the present invention, the present invention also provides the semiconductor device that method is according to the embodiment of the present invention made.
Embodiment
The present invention is hereinafter described more all sidedly., the present invention can implement with a lot of different modes, and should not be counted as in the embodiment that is limited to this paper statement.On the contrary, it is in order to make the disclosure more comprehensive thoroughly that these embodiments are provided, and scope of the present invention is fully pass on to those skilled in the art.
Be appreciated that, when element or the layer be called as another element or the layer " above " time, can be directly at another element or above the layer, be connected to another element or layer, perhaps be bonded to another element or layer, perhaps can have intermediary element or layer to exist.On the contrary, when element is known as " directly at another element or above the layer ", " being connected directly to another element or layer ", when perhaps " directly being bonded to another element or layer ", there are not intermediary element or layer.Identical numeral is represented components identical all the time.Used in the present invention " and/or " comprise that one or more are about listing any and all combinations of project.
Term of the present invention only is in order to describe the purpose of specific implementations, is not to limit the present invention.Unless context clearly demonstrates in addition, singulative used in the present invention " " also comprises plural form.It is also understood that, it is feature, integer (integer), step, operation, element and/or the composition that there is statement in expression that the term that is used for this instructions " contains ", and does not get rid of existence or add one or more further features, integer, step, operation, element, composition and/or its combination.
Unless otherwise defined, all terms used in the present invention (comprising technology and scientific terminology) have identical meanings with those skilled in the art's common sense.It is also understood that, for example the term that defines in normally used dictionary should be interpreted as having the implication of the aggregatio mentium in the context with correlation technique, and should not do to idealize or feel too formal explanation, unless expression in the present invention is exactly this meaning.
The present invention is to provide hard mask compositions, said composition can form unreacting material and the low-molecular-weight secondary product with minimum, and therefore can improve the performance of the photoresist figure that is formed by this hard mask layer.When without wishing to be bound to any theory, can believe that hydroxyl in unreacted raw material and/or low-molecular-weight secondary product can be physically and/or the character of the photoresist layer that contacts with hard mask layer of influence chemically.In the time of can believing the heating hard mask film, unreacted raw material and low molecular weight substance are owing to the low surface that trends towards migrating to film of its molecular weight.Therefore, unreacted raw material and/or low molecular weight substance can interact with the photoresist layer, and can make the character variation of photoresist layer.It is more serious that this problem can become when film thickness increases.
Therefore, according to the embodiment of the present invention, can after polycondensation, purify, removing unreacted raw material and low-molecular-weight secondary product, and can prepare polymkeric substance with relatively low polydispersity.When such polymkeric substance is used as the hard mask of resist lower membrane, can form the photoresist figure that needs.
The present invention uses:
Straight chain, side chain or the cyclic hydrocarbon group of the unit price of 1-12 carbon atom of term " alkyl " expression.In some embodiments, alkyl can be " low alkyl group (loweralkyl) " that wherein has 1-4 alkyl.For example, low alkyl group can comprise methyl, ethyl, propyl group, isopropyl, butyl and isobutyl.Term C
xAlkyl represents to have the alkyl of x carbon atom, and therefore, term C
1-C
6Alkyl represents to have any alkyl of 1-6 carbon atom.
Term " aryl " expression unit price aromatic group can randomly comprise 1-3 additional ring (additional ring fused thereto) (for example naphthenic base) that condenses with it.Aromatic ring can randomly not be substituted or by for example replacements such as one or more (for example one, two or three) halogen, alkyl, aryl.Typical aromatic yl group can comprise phenyl, xenyl, naphthyl etc.
Term aralkyl is represented by the defined alkyl of the present invention of the defined aryl replacement of the present invention.Typical aralkyl comprises benzyl, phenethyl, phenylpropyl, menaphthyl etc.
The term acetoxyl group represents-OC (=O) CH
3Group.
The term oxime is represented-the C=NOH group.
In some embodiments of the present invention, hard mask compositions can comprise the organosilane polymer by the prepared in reaction of the compound of one or more formulas I,
Si(OR
1)(OR
2)(OR
3)R
4 (I)
Wherein, R
1, R
2And R
3Can be alkyl, acetoxyl group or oxime independently of one another; And R
4Can be hydrogen, alkyl, aryl or aralkyl; And wherein organosilane polymer can have about 1.1 to about 2 polydispersity.In addition, in some embodiments, R
1, R
2, R
3And/or R
4Can be C
1-C
5Alkyl.
In some embodiments of the present invention, be antireflecting by the formed hard mask layer of the composition of embodiments of the present invention.In some embodiments of the present invention, R
4It can be phenyl.Phenyl can show absorption spectrum in the DUV zone, and this is useful in forming the antireflection hard mask material.In addition, owing to can pass through wherein R
4Be the formula I compound of phenyl and R wherein
4Control the amount of phenyl for the formula I compound that does not have active group in the DUV zone, therefore can be provided in certain wavelengths and have the absorbance that needs and the hard mask compositions of refractive index.
In some embodiments of the present invention, in hard mask compositions, can contain solvent such as organic solvent.Can use single solvent or mixed solvent.When using the mixed solvent of two or more solvents in some embodiments, wherein a kind of solvent is a high boiling solvent.High boiling solvent can reduce or prevent the formation of pore, and makes film with slower speed drying, can improve the flatness of film like this.Term used in the present invention " high boiling solvent " refers to and can be lower than coating, drying and solidify the solvent that evaporates under the temperature of hard mask compositions temperature of the present invention.
In some embodiments of the present invention, organosilane polymer can prepare in the presence of acidic catalyst in the reaction by one or more formulas (I) compound.In some embodiments, acidic catalyst can comprise at least a nitric acid, sulfuric acid, a hydration p-toluenesulfonic acid, dithyl sulfate, 2,4,4,6-tetrabromo cyclohexyl dienone, benzoin tosylate, 2-nitrobenzyl tosylate and organic sulfonic acid Arrcostab.The hydrolysis or the polycondensation reaction that form organosilane polymer can suitably be controlled by the type, consumption and the adding method that change acidic catalyst.
In some embodiments of the present invention, organosilane polymer can prepare by about 1 reaction to one or more formulas I compound of about 99 weight portions to the acidic catalyst of about 5 weight portions about 0.001.
In some embodiments of the present invention, the organosilane polymer that is formed by the reaction of one or more formulas I compound can have the structure of formula II,
R wherein
4, i.e. R
4', R
4", R
4" ' and R
4" " can be identical or different, and can be hydrogen, alkyl (C for example independently
1-C
5Alkyl), aryl or aralkyl, and n can be a positive integer.For example, in some embodiments, R
4' and R
4" can be alkyl and R
4" ' and R
4" " can be aryl.In addition, each repetitive can comprise different R
4Group is supposed each R
4Be hydrogen, alkyl, aryl or aralkyl.Therefore, in some repetitives of the organosilane that formula II represents, R
4' can be alkyl, and in other repetitive, R
4' can be aryl.Therefore, the potpourri of different formula I compounds can react the organosilane polymer that forms formula II.
In some embodiments, organosilane polymer can have about 1000 molecular weight to about 50000 gram/moles.In some embodiments, organosilane polymer can have about 1.1 to about 2 polydispersity.
In some embodiments of the present invention, hard mask compositions based on 100 weight portions, organosilane polymer can be present in the hard mask compositions with about 1 content to about 50 weight portions, and in some embodiments, exists with about 1 content to about 30 weight portions.
When needing, can randomly comprise the component that other is suitable according to the hard mask compositions of embodiment of the present invention, for example one or more in crosslinking chemical, free radical stabilizer and the surfactant.
In some embodiments of the present invention, the method that forms semiconductor devices comprises that (a) forms material layer in substrate; (b) on described material layer, form organic hard mask layer; (c) on described organic hard mask layer, form the hard mask of antireflection by antireflective hardmask composition of the present invention; (d) on described antireflection hard mask layer, form the photosensitive imaging layer; (e) mode with figure is exposed to described imaging layer under the radiation, to form the figure in radiant exposure zone in described imaging layer; (f) selectively remove the described imaging layer of part, antireflection hard mask layer and organic hard mask layer, to expose the described material layer of part; And (h) expose portion of the described material layer of etching, to form the material layer of patterning.In some embodiments, can be by selectively removing the described imaging layer of part with the described antireflection hard mask layer of expose portion, selectively remove part antireflection hard mask layer with the described organic hard mask layer of expose portion; And selectively remove the described organic hard mask layer of part and selectively remove the described imaging layer of part, described anti-reflecting layer and organic hard mask layer with the described material layer of expose portion.
In some embodiments of the present invention, provide the semiconductor device made from method of the present invention.
For example, the compositions and methods of the invention can be applied to form the material layer structures of patterning, as metal wiring circuit, contact hole and biasing (biases), insulated part, as Damascus groove (damascene trenches) and shallow-trench isolation, and the groove that is used for capacitor arrangement, as be used for the groove of designing integrated circuit device.The compositions and methods of the invention particularly can be used to form oxide, nitride, polysilicon and the chromium oxide of patterning.
Hereinafter, the present invention will be described in more detail with reference to the following example., providing these embodiment is to be used to illustrate purpose of the present invention, and should not think limitation of the scope of the invention.
Embodiment
Preparation example 1
In 1 liter of four neck flask that mechanical stirrer, condenser, 300 milliliters of tap funnels and nitrogen delivery pipe are housed with 8.31 gram (0.05 moles) 1, two (methoxy) benzene of 4-, 0.154 gram (0.001 mole) dithyl sulfate and 200 gram gamma-butyrolactons stirred 10 minutes, simultaneously nitrogen were sent in the flask.With 28.02 gram (0.08 moles) 4 of 200 gram gamma-butyrolactons, 4-(9-fluorenylidene) two phenol solutions slowly dripped 30 minutes.With this potpourri reaction 12 hours.After reaction finished, water removed disacidify, then adopted evaporator to concentrate.Subsequently, concentrate is obtained the solution of 15 weight % in MAK/ methyl alcohol (weight ratio is 4: 1) with MAK (MAK) and methyl alcohol dilution.The solution that obtains is thus moved in 3 liters of separating funnels, add normal heptane then,, obtain the resin (M that needs to remove the low molecular weight compound that contains unreacted monomer
w=12000, polydispersity=2.0, n=23).
Be dissolved in 9 gram PGMEAs and filtration by low polyhydroxy crosslinking agent (Powderlink 1174) and 2 milligrams of pyridine tosilate that constitutional repeating unit shown below constitutes the above-mentioned resin of 0.8 gram, 0.2 gram, with the preparation sample solution,
The structure of Powderlink 1174
Sample solution is spin-coated on the silicon chip and, makes the thick film of 1500 dusts 200 ℃ of bakings 60 seconds.
Embodiment 1
In 10 liter of four neck flask of mechanical stirrer, condenser, tap funnel and nitrogen delivery pipe is housed, 2100 gram methyltrimethoxy silane and 340 gram phenyltrimethoxysila,e is dissolved among the 5600 gram PGMEA, and adds 925 gram salpeter solutions (1000ppm).Gained solution after 1 hour, is under reduced pressure removed the methyl alcohol and the part PGMEA of formation 60 ℃ of reactions.To react and continue to keep temperature of reaction in a week simultaneously at 50 ℃.After reaction finishes, the hexane of appropriate amount is added to obtains precipitation in the reaction solution.With sedimentation and filtration, be scattered in the hexane again and filtration once more.To in hexane, disperse subsequent filtration to repeat twice again, so that the solid polymer (M that needs to be provided
w=15000, polydispersity=1.50).10 these polymer dissolution of gram are prepared sample solution in 100 gram PGMEA and 100 gram ethyl lactates.
Sample solution is spin-coated on the film of being made by preparation example 1, and made the thick film of 600 dusts in 60 seconds 200 ℃ of bakings.
Embodiment 2
In 10 liter of four neck flask of mechanical stirrer, condenser, tap funnel and nitrogen delivery pipe is housed, 2100 gram methyltrimethoxy silane and 340 gram phenyltrimethoxysila,e is dissolved among the 5600 gram PGMEA, and adds 925 gram salpeter solutions (1000ppm).Gained solution after 1 hour, is under reduced pressure removed the methyl alcohol and the part PGMEA of formation 60 ℃ of reactions.To react and continue to keep temperature of reaction in a week simultaneously at 50 ℃.After reaction finishes, the hexane of appropriate amount is added to reaction solution obtains precipitation.With sedimentation and filtration, be scattered in the hexane again and filtration once more, so that the solid polymer (M that needs to be provided
w=14000, polydispersity=1.95).10 these polymer dissolution of gram are prepared sample solution in 100 gram PGMEA and 100 gram ethyl lactates.
Sample solution is spin-coated on the film of being made by preparation example 1, and made the thick film of 600 dusts in 60 seconds 200 ℃ of bakings.
Comparative Examples 1
In 10 liter of four neck flask of mechanical stirrer, condenser, tap funnel and nitrogen delivery pipe is housed, 2100 gram methyltrimethoxy silane and 340 gram phenyltrimethoxysila,e is dissolved among the 5600 gram PGMEA, and adds 925 gram salpeter solutions (1000ppm).Gained solution after 1 hour, is under reduced pressure removed the methyl alcohol and the part PGMEA of formation 60 ℃ of reactions.To react and continue to keep temperature of reaction in a week simultaneously at 50 ℃.After reaction finishes, the hexane of appropriate amount is added to reaction solution obtains precipitation.With precipitate and separate, but be not scattered in once more in the hexane, the solid polymer (M that needs is provided
w=15000, polydispersity=4.60).10 these polymer dissolution of gram are prepared sample solution in 100 gram PGMEA and 100 gram ethyl lactates.
Sample solution is spin-coated on the film of being made by preparation example 1, and made the thick film of 600 dusts in 60 seconds 200 ℃ of bakings.
With embodiment 1 and 2 and Comparative Examples 1 made polymer solution be coated in separately on the silicon chip, with the preparation film.Measure the refractive index (n) and the extinction coefficient (k) of film with ellipsometer (J.A.Woolam).The results are shown in table 1.
Table 1
The photoresist that will be used for ArF is coated in by embodiment 1 and 2 and each wafer of making of Comparative Examples 1,110 ℃ of bakings 60 seconds, with ArF exposure system (ASML1250, the FN705.0 activity, NA 0.82) exposure, and develop with TMAH aqueous solution (2.38 weight %), form the line of 80 nanometers and (line and space) figure at interval.Observe the line and interval figure of 80 nanometers with FE-SEM, and gained be the results are shown in table 2.The exposure latitude (exposurelatitude) that measurement changes according to exposure energy is border and according to the depth of focus (DoF) border from the variable in distance of light source (EL).The results are shown in table 2.
Table 2
Above description obviously, the hard mask compositions of use embodiment of the present invention can improve the repeatability of figure, be enough to adhere on the resist, behind the exposure resist, can enough resist the developing solution of use, and can reduce because the film loss that plasma etching causes.
Disclose the preferred embodiment of the present invention although be used for the purpose of illustration, person of skill in the art will appreciate that, under the disclosed scope and spirit of the present invention, various changes, increase and replacement all are possible in not leaving subsidiary claims.
Claims (11)
1. hard mask compositions, said composition contains the organosilane polymer by the prepared in reaction of one or more formulas I compound,
Si(OR
1)(OR
2)(OR
3)R
4 (I)
Wherein, R
1, R
2And R
3Be alkyl independently of one another; And R
4Be selected from the group of forming by hydrogen, alkyl, aryl and aralkyl; Described alkyl is represented straight chain, side chain or the cyclic hydrocarbon group of the unit price of 1-12 carbon atom; Described aralkyl is represented the alkyl that described alkyl is replaced by aryl; And
Wherein, described organosilane polymer has 1.1 to 2 polydispersity.
2. hard mask compositions according to claim 1, wherein, described R
1, R
2And R
3Be C independently of one another
1-C
5Alkyl; And described R
4Be selected from by hydrogen, C
1-C
5In the group that alkyl, aryl and aralkyl are formed.
3. hard mask compositions according to claim 1, wherein, the reaction of described one or more formulas I compound is carried out in the presence of acidic catalyst.
4. hard mask compositions according to claim 3, wherein, described acidic catalyst contains at least a being selected from by nitric acid, sulfuric acid, a hydration p-toluenesulfonic acid, dithyl sulfate, 2,4,4, the acid in the group that 6-tetrabromo cyclohexyl dienone, benzoin tosylate, 2-nitrobenzyl tosylate and organic sulfonic acid Arrcostab are formed.
5. hard mask compositions according to claim 3, wherein, described organosilane polymer is that one or more formulas (I) compound by 1 to 99 weight portion reacts in the presence of the acidic catalyst of 0.001 to 5 weight portion and prepares.
6. hard mask compositions according to claim 1, wherein, described organosilane polymer contains the structure of formula II,
Wherein, R
4', R
4", R
4' " and R
4" " is selected from the group of being made up of hydrogen, alkyl, aryl and aralkyl independently of one another; Described alkyl is represented straight chain, side chain or the cyclic hydrocarbon group of the unit price of 1-12 carbon atom; Described aralkyl is represented the alkyl that described alkyl is replaced by aryl.
7. hard mask compositions according to claim 1, wherein, described organosilane polymer has the molecular weight of 1000 to 50000 gram/moles.
8. hard mask compositions according to claim 1, said composition also contains organic solvent.
9. method that forms semiconductor devices, this method comprises
In substrate, form material layer;
On described material layer, form organic hard mask layer;
On described organic hard mask layer, form the antireflection hard mask layer by the described antireflective hardmask composition of claim 1;
On described antireflection hard mask layer, form the photosensitive imaging layer;
Mode with figure is exposed to described imaging layer under the radiation, to form the figure in radiant exposure zone in described imaging layer;
Optionally remove the described imaging layer of part, the hard mask of described antireflection and described organic hard mask layer, to expose the described material layer of part; And
The described material layer of the described exposed portions of etching is to form patterned material layer.
10. method according to claim 9, wherein, the step of optionally removing the described imaging layer of part, described antireflection hard mask layer and described organic hard mask layer comprises
Optionally remove the described imaging layer of part, with expose portion antireflection hard mask layer,
Optionally remove the described antireflection hard mask layer of part, with the organic hard mask layer of expose portion, and
Optionally remove the described organic hard mask layer of part, with the described material layer of expose portion.
11. semiconductor device of making by the described method of claim 9.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020060026211 | 2006-03-22 | ||
| KR20060026211 | 2006-03-22 | ||
| KR10-2006-0026211 | 2006-03-22 | ||
| KR10-2006-0049341 | 2006-06-01 | ||
| KR1020060049341 | 2006-06-01 | ||
| KR1020060049341A KR20070095736A (en) | 2006-03-22 | 2006-06-01 | Hardmask composition coated under photoresist comprising organosilane polymer and process of producing integrated circuit devices using thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101042533A CN101042533A (en) | 2007-09-26 |
| CN101042533B true CN101042533B (en) | 2010-05-19 |
Family
ID=38802907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007100075135A Active CN101042533B (en) | 2006-03-22 | 2007-01-30 | Organosilane hardmask compositions and methods of producing semiconductor devices using the same |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR20070095736A (en) |
| CN (1) | CN101042533B (en) |
| TW (1) | TWI341959B (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101288572B1 (en) * | 2008-12-17 | 2013-07-22 | 제일모직주식회사 | Hardmask Composition Coated under Photoresist with Improved Storage Stability |
| KR101266291B1 (en) | 2008-12-30 | 2013-05-22 | 제일모직주식회사 | Resist underlayer composition and Process of Producing Integrated Circuit Devices Using the Same |
| KR101400182B1 (en) * | 2009-12-31 | 2014-05-27 | 제일모직 주식회사 | Photoresist underlayer composition and method of manufacturing semiconductor device by using the same |
| KR101344795B1 (en) * | 2009-12-31 | 2013-12-26 | 제일모직주식회사 | Resist underlayer composition and Process of Producing Integrated Circuit Devices Using the Same |
| KR101441563B1 (en) * | 2011-12-30 | 2014-09-18 | 영창케미칼 주식회사 | Thermosetting Silicon Resin for Multifunctional Antireflective Coating and Antireflective Coating manufactured thereof |
| KR101556276B1 (en) * | 2012-12-28 | 2015-09-30 | 제일모직 주식회사 | Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030031789A1 (en) * | 1998-03-20 | 2003-02-13 | Bedwell William B. | Organosiloxanes |
| WO2004090965A2 (en) * | 2003-04-02 | 2004-10-21 | Dow Global Technologies Inc. | Organosilicate resin formulation for use in microelectronic devices |
| CN1585097A (en) * | 2003-08-22 | 2005-02-23 | 国际商业机器公司 | Antireflective hardmask and uses thereof |
| CN1619415A (en) * | 2003-10-06 | 2005-05-25 | 国际商业机器公司 | Silicon-containing compositions for spin-on arc/hardmask materials |
| CN1671772A (en) * | 2002-06-03 | 2005-09-21 | 霍尼韦尔国际公司 | Organosiloxanes |
-
2006
- 2006-06-01 KR KR1020060049341A patent/KR20070095736A/en not_active Application Discontinuation
- 2006-12-22 TW TW095148412A patent/TWI341959B/en active
-
2007
- 2007-01-30 CN CN2007100075135A patent/CN101042533B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030031789A1 (en) * | 1998-03-20 | 2003-02-13 | Bedwell William B. | Organosiloxanes |
| CN1671772A (en) * | 2002-06-03 | 2005-09-21 | 霍尼韦尔国际公司 | Organosiloxanes |
| WO2004090965A2 (en) * | 2003-04-02 | 2004-10-21 | Dow Global Technologies Inc. | Organosilicate resin formulation for use in microelectronic devices |
| CN1585097A (en) * | 2003-08-22 | 2005-02-23 | 国际商业机器公司 | Antireflective hardmask and uses thereof |
| CN1619415A (en) * | 2003-10-06 | 2005-05-25 | 国际商业机器公司 | Silicon-containing compositions for spin-on arc/hardmask materials |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20070095736A (en) | 2007-10-01 |
| TWI341959B (en) | 2011-05-11 |
| CN101042533A (en) | 2007-09-26 |
| TW200736840A (en) | 2007-10-01 |
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