CN1873532A - Polymer for immersion lithography, photoresist composition containing the same, method of manufacturing a semiconductor device, and semiconductor device - Google Patents
Polymer for immersion lithography, photoresist composition containing the same, method of manufacturing a semiconductor device, and semiconductor device Download PDFInfo
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- CN1873532A CN1873532A CNA2005101363003A CN200510136300A CN1873532A CN 1873532 A CN1873532 A CN 1873532A CN A2005101363003 A CNA2005101363003 A CN A2005101363003A CN 200510136300 A CN200510136300 A CN 200510136300A CN 1873532 A CN1873532 A CN 1873532A
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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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0395—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having a backbone with alicyclic moieties
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/265—Selective reaction with inorganic or organometallic reagents after image-wise exposure, e.g. silylation
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- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
A polymer for immersion lithography comprising a repeating unit represented by Formula 1 and a photoresist composition containing the same. A photoresist film formed by the photoresist composition of the invention is highly resistant to dissolution, a photoacid generator in an aqueous solution for immersion lithography, thereby preventing contamination of an exposure lens and deformation of the photoresist pattern by exposure.
Description
Technical field
The disclosure relates to a kind of polymkeric substance and a kind of photo-corrosion-resisting agent composition that contains it that is used for immersion lithographic, to obtain fine pattern in the manufacturing of semiconductor devices.
Background technology
Presently used photoetching technique is for adopting the dry lithography technology of exposure system, and fill with air at the interval in this exposure system between exposure lens and wafer.In order to use dry lithography to develop the device of 60nm resolution, need to use such as F
2The new exposure system of the light source of laser (157nm) or extreme ultraviolet (EUV) laser.Yet, when using F
2Be difficult to development film (pellicle) during laser, and when using EUV laser, be difficult to develop mask and light source.
In order to overcome the problems referred to above, developed immersion lithographic.
In immersion lithographic, suitable aqueous solution is filled the interval between projecting lens and the wafer, thereby increases the optical numerical value aperture corresponding to this solution refractive index.The actual wavelength of the light source in the solution equals by with the wavelength of the airborne light source value that refractive index calculated divided by this solution.For example, if reflectivity be 1.44 water as medium, then the 193nm wavelength Conversion with the ArF light source is 134nm.This with have such as F when using
2The effect that the light source of the shorter wavelength of laser (157nm) increases resolution is identical.
Yet, because the interval between projecting lens and the wafer is not to fill air and fill aqueous solution in the conventional immersion lithographic, so existing light acid propellant may be dissolved in this aqueous solution in the photoresist, cause exposure lens to be polluted and the photoresist pattern deformation.
Summary of the invention
The disclosure provides a kind of polymkeric substance that is used for immersion lithographic, and it prevents that in immersion lithographic process light acid propellant is dissolved in the aqueous solution that is used for immersion lithographic.This paper also discloses a kind of photo-corrosion-resisting agent composition that contains this polymkeric substance.
In addition, disclose the disclosed photo-corrosion-resisting agent composition of a kind of use herein and form the photoresist method of patterning, and a kind of semiconductor devices of making by disclosed method.
Description of drawings
In order more completely to understand the present invention, should be with reference to following detailed and accompanying drawing, in the accompanying drawing:
Fig. 1 a is the cut-open view of shower type immersion lithographic exposer used in the explanation disclosure;
Fig. 1 b is the cut-open view of shower type immersion lithographic exposer used in the explanation disclosure;
Fig. 1 c is the cut-open view of immersion type immersion lithographic exposer used in the explanation disclosure;
Fig. 2 a is for deriving from the NMR spectrum of the polymkeric substance for preparing embodiment 1;
Fig. 2 b is for deriving from the NMR spectrum of the polymkeric substance for preparing embodiment 2;
Fig. 3 a is the photo that derives from the photoresist pattern of embodiment 3;
Fig. 3 b is the photo that derives from the photoresist pattern of embodiment 4; And
Fig. 4 is the photo that derives from the photoresist pattern of Comparative Examples.
Instructions, drawings and Examples are illustrative, and do not mean that the restriction disclosure is in specific embodiments described herein.
The symbol description of each element in the accompanying drawing
10 wafers
20 are used for the solution of immersion lithographic
30 immersion lens unit
40 wafer station
50 projecting lens unit
Embodiment
Provide a kind of light acid that is used for immersion lithographic that is obtained by direct combined light acid producing agent and photoresist polymkeric substance to produce polymkeric substance.This polymkeric substance comprises the repetitive shown in the formula 1:
[formula 1]
X in the formula
1Be C
1-C
10Alkylidene, sulphur or oxygen; And
A is that light acid produces group, and any suitable light acid producing agent can unrestrictedly use.In this article, " light acid produces group " is meant by the acidic group that exposes.Preferably, X
1Be C
1-C
3Alkylidene comprises that the repetitive of A is represented by formula 1a:
[formula 1a]
X in the formula
1Be C
1-C
10Alkylidene, sulphur or oxygen; And
R
1Be straight or branched C
1-C
10Alkyl, perhaps the straight or branched C that partly or entirely replaces through halogen
1-C
10Alkyl.
Preferably, the repetitive of being represented by formula 1a is represented by formula 1b:
[formula 1b]
In the polymkeric substance of formula 1a, the component that is used as the light acid producing agent is sulfonic group (SO
3 -), sulfonic acid (SO wherein
3H) produce by exposure.
According to this method, by directly will preventing that the light acid producing agent is dissolved in the aqueous solution that is used for immersion lithographic between exposure period as the moiety combinations of water-based light acid producing agent compound to organic photoresist formulation polymkeric substance.
Preferably, this polymkeric substance comprises the polymer repeating unit by formula 2 or formula 3 expressions:
[formula 2]
X in the formula
1, X
2And X
3Be C separately
1-C
10Alkylidene, sulphur or oxygen;
R
1Be straight or branched C
1-C
10Alkyl, perhaps the straight or branched C that partly or entirely replaces through halogen
1-C
10Alkyl;
R
2Be straight or branched C
1-C
10Alkylidene, perhaps the straight or branched C that partly replaces through halogen
1-C
10Alkylidene;
R
3Be sour destabilization protecting group; And
The relative quantity of a: b: c: d with weight portion count 100: 10～40: 30～70: 10～40.
[formula 3]
X in the formula
1Be C
1-C
10Alkylidene, sulphur or oxygen;
R
1Be straight or branched C
1-C
10Alkyl, perhaps the straight or branched C that partly or entirely replaces through halogen
1-C
10Alkyl;
R
2Be sour destabilization protecting group;
R
3And R
4Be hydrogen or methyl separately; And
The relative quantity of a: b: c: d counts 5～30 with weight portion: 100: 5～30: 5～70.
" sour destabilization protecting group " group for being separated by acid.When sour destabilization protecting group was incorporated into photoresist, it prevented that photoresist is dissolved in the alkaline development solution.Yet when sour destabilization protecting group was separated by the acid that produces by exposure, this photoresist can be dissolved in the alkaline development solution.
Can use any suitable sour destabilization protecting group.Suitable example is disclosed in USP5212043 (on May 18th, 1993), WO 97/33198 (on September 12nd, 1997), WO96/37526 (on November 28th, 1996), EP 0794458 (on September 10th, 1997), EP0789278 (on August 13rd, 1997), USP 5750680 (on May 12nd, 1998), USP6051678 (on April 18th, 2000), GB 2345286 A (on July 5th, 2000), USP6132926 (on October 17th, 2000), USP 6143463 (on November 7th, 2000), USP6150069 (on November 21st, 2000), USP 6180316 B1 (January 30 calendar year 2001), USP6225020 B1 (May 1 calendar year 2001), among USP 6235448 B1 (May 22 calendar year 2001) and the USP6235447 B1 (May 22 calendar year 2001), wherein each openly is incorporated herein by reference.
Preferably, sour destabilization protecting group is selected from: the tert-butyl group, oxinane-2-base, 2-methyl oxinane-2-base, tetrahydrofuran-2-base, 2-methyltetrahydrofuran-2-base, 1-methoxy-propyl, 1-methoxyl-1-Methylethyl, 1-ethoxycarbonyl propyl, 1-ethoxy-1-Methylethyl, 1-methoxy ethyl, 1-ethoxyethyl group, tert-butoxy ethyl, 1-isobutoxy ethyl and 2-acetyl group peppermint (acetylment)-1-base.
Preferably, the polymer repeating unit of formula 2 or formula 3 is represented by formula 2a or formula 3a respectively:
[formula 2a]
The relative quantity of a in the formula: b: c: d with weight portion count 100: 10～40: 30～70: 10～40.
[formula 3a]
The relative quantity of a in the formula: b: c: d counts 5～30 with weight portion: 100: 5～30: 5～70.
Disclosed polymkeric substance comprises the polymer repeating unit of straight chain.If necessary, disclosed polymkeric substance can further comprise another monomer or adjuvant.
And, a kind of photo-corrosion-resisting agent composition that contains disclosed polymkeric substance and organic solvent is provided.If necessary, disclosed photo-corrosion-resisting agent composition can further contain light acid producing agent, photoresist polymkeric substance and/or adjuvant.Preferably, disclosed photo-corrosion-resisting agent composition is used for immersion lithographic.
The photoresist polymkeric substance can be chemical amplifying type photoresist polymkeric substance.Preferably, this photoresist polymkeric substance is the polymkeric substance that comprises by the polymer repeating unit of formula 4 expressions:
[formula 4]
The relative quantity of e in the formula: f: g with weight portion count 100: 5～30: 40～70: 10～40.
Can adopt any suitable organic solvent, the example of The suitable solvent is disclosed in the above-mentioned list of references.Preferred organic is selected from: 3-methoxypropionic acid methyl esters, 3-ethoxyl ethyl propionate, propylene glycol methyl ether acetate, cyclohexanone, 2-heptanone, ethyl lactate and composition thereof.Preferably, based on the photoresist polymkeric substance that is used for immersion lithographic, this organic solvent exists with the amount of 500～3000 weight portions.
When further comprising the photoresist polymkeric substance, based on the photo-corrosion-resisting agent composition of 100 weight portions, polymkeric substance of the present invention preferably exists with the amount of 5～20 weight portions.
The use of disclosed polymkeric substance is not limited to immersion lithographic, and it can be used for general dry lithography technology.In the prior art, when the painting photoresist composition formed light actuating resisting corrosion film, the light acid producing agent was included in the photo-corrosion-resisting agent composition as independent molecule, and is distributed in the photo-corrosion-resisting agent composition unevenly.As a result, even unexposed light actuating resisting corrosion film also can develop by using low-level exposure energy.Yet, because the light acid producing agent directly with polymkeric substance of the present invention in organic polymer make up, so this light acid producing agent distribute equably, thereby prevent that unexposed part from developing under low-level exposure energy.
In addition, provide a kind of method of making semiconductor devices, this method may further comprise the steps:
(a) above-mentioned photo-corrosion-resisting agent composition is coated down on the coating to form light actuating resisting corrosion film;
(b) this light actuating resisting corrosion film that exposes;
(c) develop this light actuating resisting corrosion film to obtain the photoresist pattern through exposing; And
(d) this photoresist pattern is carried out etching process with this time of etching coating as etching mask, thereby obtain coating pattern down.
Preferably, the exposure sources that is used for immersion lithographic carries out step of exposure (b).Above method can further be included in this step of exposure (b) before the soft baking step or at this step of exposure (b) back baking step afterwards.Preferably, this baking step carries out under 70～200 ℃ temperature.
The light source of step (b) is preferably selected from: F
2(157nm), ArF (193nm), KrF (248nm), E-bundle, EUV (far ultraviolet) and ion beam, and step of exposure (b) is preferably with about 1～100mJ/cm
2Exposure energy carry out.
Step (c) can be carried out in alkaline development solution, and this solution is preferably TMAH (tetramethylammonium hydroxide) aqueous solution of 0.5～5% weight.
The exposer that is used for immersion lithographic generally includes immersion lens unit, wafer station and projecting lens unit.This immersion lens unit is configured to the recovery unit of the aqueous solution that comprises outer cover unit, feed unit and be used for immersion lithographic.In the step of exposure process, the aqueous solution that will be used for immersion lithographic is applied to the immersion lens unit.
The exposer that is used for immersion lithographic is preferably any of shower type, shower type or immersion type exposer.
Fig. 1 a illustrates a kind of shower type exposer that is used for immersion lithographic that comprises immersion lens unit 30, so that with the whole surface of aqueous solution 20 cover wafers 10 that are used for immersion lithographic.
Fig. 1 b illustrates a kind of shower type exposer that is used for immersion lithographic that comprises immersion lens unit 30, and it holds the aqueous solution 20 that is used for immersion lithographic at place, projecting lens unit 50 bottoms.
Fig. 1 c illustrates a kind of immersion type exposer that is used for immersion lithographic that comprises immersion lens unit 30, and the wafer station 40 that wafer 10 wherein is installed is immersed in the aqueous solution 20 that is used for immersion lithographic.
And, a kind of semiconductor devices of making by disclosed method also is provided.
Embodiment
To describe the present invention in detail with reference to following examples, embodiment is intended to limit the present invention.
Preparation embodiment 1: synthetic poly-(dicyclo [2,2,1] heptan-5-alkene-2-carboxylic acid tert-butyl ester/dicyclo [2,2,1] heptan-5-alkene-2-carboxylic acid 2-hydroxyl ethyl ester/N-[(perfluor fourth sulfonyl) oxygen base]-norcamphane (norbonane)-2,3-dicarboxyl acid imide/maleic anhydride)
With dicyclo [2; 2; 1] heptan-5-alkene-2-carboxylic acid tert-butyl ester (19.41g), dicyclo [2; 2; 1] heptan-5-alkene-2-carboxylic acid 2-hydroxyl ethyl ester (5.4g), N-[(perfluor fourth sulfonyl) the oxygen base]-norcamphane-2; 3-dicarboxyl acid imide (9.5g), maleic anhydride (14g) and as the AIBN (2,2 ' azoisobutyronitrile) of polymerization initiator (1.35g) be dissolved in THF (tetrahydrofuran) (40g) in.Make the gained potpourri 67 ℃ of following polymerizations 24 hours.After reaction, in ether, obtain sediment, filter, and dehydration in a vacuum, thereby the synthetic formula 2a compound (referring to the NMR spectrum of Fig. 2 a) that is used for immersion lithographic.
Preparation embodiment 2: synthetic poly-(the hot sulfonyl of methyl methacrylate (methyl methacrylic acid)/tert-butyl acrylate/maleic anhydride/N-[(perfluor) oxygen base]-norcamphane-2,3-dicarboxyl acid imide)
With methyl methacrylate (2.0g), tert-butyl acrylate (9.0g), maleic anhydride (2.0g), the hot sulfonyl of N-[(perfluor) the oxygen base]-norcamphane-2; 3-dicarboxyl acid imide) (2.0g) and as the AIBN (2,2 ' azoisobutyronitrile) of polymerization initiator (0.3g) is dissolved in the acetone (45g).Make the gained potpourri 67 ℃ of following polymerizations 6 hours.After polymerization, in water, obtain sediment, filter, and dehydration in a vacuum, thereby the compound of the formula of acquisition 3a (productive rate: 48%, referring to the NMR spectrum of Fig. 2 b).
Preparation embodiment 3: synthetic poly-(dicyclo [2,2,1] heptan-5-alkene-2-carboxylic acid tert-butyl ester/dicyclo [2,2,1] heptan-5-alkene-2-carboxylic acid 2-hydroxyl ethyl ester/maleic anhydride)
With dicyclo [2,2,1] heptan-5-alkene-2-carboxylic acid tert-butyl ester (23.57g), dicyclo [2,2,1] heptan-5-alkene-2-carboxylic acid 2-hydroxyl ethyl ester (3.90g), maleic anhydride (14g) and (0.55g) be dissolved among the THF (20g) as the AIBN (2,2 ' azoisobutyronitrile) of polymerization initiator.Make the gained potpourri 67 ℃ of following polymerizations 24 hours.After polymerization, in ether, obtain sediment, filter, and dehydration in a vacuum, thereby the compound of acquisition formula 4 (productive rate: 76%).
Embodiment 1: prepare the disclosed photo-corrosion-resisting agent composition (1) that is used for immersion lithographic
The formula 2a polymkeric substance (1g) and the triethanolamine (0.006g) that will prepare embodiment 1 acquisition certainly are dissolved in the propylene glycol methyl ether acetate (13g), thereby obtain the disclosed photo-corrosion-resisting agent composition that is used for immersion lithographic.
Embodiment 2: prepare the disclosed photo-corrosion-resisting agent composition (2) that is used for immersion lithographic
Will be as the preparing polymkeric substance (0.1g) that embodiment 2 obtains certainly, be dissolved in the propylene glycol methyl ether acetate (13g) of light acid producing agent as the polymkeric substance (1g) and the triethanolamine (0.001g) that embodiment 3 obtains that prepare certainly of photoresist polymkeric substance, thus the disclosed photo-corrosion-resisting agent composition that is used for immersion lithographic obtained.
Embodiment 3: form disclosed photoresist pattern (1)
The photo-corrosion-resisting agent composition that is used for immersion lithographic that will obtain from embodiment 1 is coated on wafer with the thickness of 240nm, and 130 ℃ of following soft bakings 90 seconds, thereby obtain light actuating resisting corrosion film.Then, with the wafer submerged that is coated with 3 minutes, so that observe the aqueous solution effects whether the photoresist pattern that forms by the disclosed photo-corrosion-resisting agent composition that is used for immersion lithographic can be subjected to being used for immersion lithographic.
Then, use ArF exposer this light actuating resisting corrosion film that exposes, and cured 90 seconds after down at 130 ℃.Then, it was developed 40 seconds in the TMAH of 2.38% weight aqueous solution, thereby obtain the photoresist pattern (a) referring to Fig. 3.
Shown in Fig. 3 a, this photoresist pattern is vertically to form by the disclosed photo-corrosion-resisting agent composition that is used for immersion lithographic.
Embodiment 4: form disclosed photoresist pattern (2)
Repeat the program of embodiment 3, different is, the photo-corrosion-resisting agent composition that is used for immersion lithographic that will obtain from embodiment 2 is coated on wafer with the thickness of 200nm, thereby obtains the photoresist pattern.
Shown in Fig. 3 b, this photoresist pattern is vertically to form by the disclosed photo-corrosion-resisting agent composition that is used for immersion lithographic.
Comparative Examples: form the photoresist pattern
To comprise that independently the emulsion of light acid producing agent (is made by JSR company; AR1221J) thickness with 240nm is coated on the wafer, and 130 ℃ of following soft bakings 90 seconds, thereby obtain light actuating resisting corrosion film.Then, with the wafer submerged that is coated with 3 minutes, so that observe the aqueous solution effects whether the photoresist pattern that forms by conventional photo-corrosion-resisting agent composition can be subjected to being used for immersion lithographic.
Then, use ArF exposer this light actuating resisting corrosion film that exposes, and cured 90 seconds after down at 130 ℃.Then, it was developed 40 seconds in the TMAH of 2.38% weight aqueous solution, thereby obtain photoresist pattern (referring to Fig. 4).
As shown in Figure 4, this photoresist pattern does not vertically form, but by this routine photo-corrosion-resisting agent composition distortion.
As mentioned above, vertically form the photoresist pattern with disclosed composition.Even when light actuating resisting corrosion film that forms by composition and aqueous solution Long contact time, the light acid producing agent can not be dissolved in the aqueous solution that is used for immersion lithographic yet, thereby prevent that exposure lens from polluting and the photoresist pattern deformation by exposing.
Claims (26)
1. a light acid that comprises the repetitive shown in the formula 1 produces polymkeric substance:
[formula 1]
X in the formula
1Be C
1-C
10Alkylidene, sulphur or oxygen; And
A is that light acid produces group.
2. according to the polymkeric substance of claim 1, X wherein
1Be C
1-C
3Alkylidene.
3. according to the polymkeric substance of claim 1, wherein this repetitive is represented by formula 1a:
[formula 1a]
X in the formula
1Be C
1-C
10Alkylidene, sulphur or oxygen; And
R
1Be straight or branched C
1-C
10Alkyl, perhaps the straight or branched C that partly or entirely replaces through halogen
1-C
10Alkyl.
4. according to the polymkeric substance of claim 3, X wherein
1Be C
1-C
3Alkylidene.
5. according to the polymkeric substance of claim 3, wherein this repetitive is represented by formula 1b:
[formula 1b]
6. according to the polymkeric substance of claim 3, wherein this polymkeric substance comprises the polymer repeating unit by formula 2 expressions:
[formula 2]
X in the formula
1, X
2And X
3Be C separately
1-C
10Alkylidene, sulphur or oxygen;
R
1Be straight or branched C
1-C
10Alkyl, perhaps the straight or branched C that partly or entirely replaces through halogen
1-C
10Alkyl;
R
2Be straight or branched C
1-C
10Alkylidene, perhaps the straight or branched C that partly replaces through halogen
1-C
10Alkylidene; And
R
3Be sour destabilization protecting group;
The relative quantity of a in the formula: b: c: d in weight portion, is 100: 10～40: 30～70: 10～40.
7. according to the polymkeric substance of claim 6, wherein should acid destabilization protecting group be selected from: the tert-butyl group, oxinane-2-base, 2-methyl oxinane-2-base, tetrahydrofuran-2-base, 2-methyltetrahydrofuran-2-base, 1-methoxy-propyl, 1-methoxyl-1-Methylethyl, 1-ethoxycarbonyl propyl, 1-ethoxy-1-Methylethyl, 1-methoxy ethyl, 1-ethoxyethyl group, tert-butoxy ethyl, 1-isobutoxy ethyl and 2-acetyl group peppermint-1-base.
8. according to the polymkeric substance of claim 6, wherein this polymer repeating unit is represented by formula 2a:
[formula 2a]
The relative quantity of a in the formula: b: c: d in weight portion, is 100: 10～40: 30～70: 10～40.
9. polymkeric substance according to Claim 8 wherein should acid destabilization protecting group be selected from: the tert-butyl group, oxinane-2-base, 2-methyl oxinane-2-base, tetrahydrofuran-2-base, 2-methyltetrahydrofuran-2-base, 1-methoxy-propyl, 1-methoxyl-1-Methylethyl, 1-ethoxycarbonyl propyl, 1-ethoxy-1-Methylethyl, 1-methoxy ethyl, 1-ethoxyethyl group, tert-butoxy ethyl, 1-isobutoxy ethyl and 2-acetyl group peppermint-1-base.
10. according to the polymkeric substance of claim 3, wherein this polymkeric substance comprises the polymer repeating unit by formula 3 expressions:
[formula 3]
X in the formula
1Be C
1-C
10Alkylidene, sulphur or oxygen;
R
1Be straight or branched C
1-C
10Alkyl, perhaps the straight or branched C that partly or entirely replaces through halogen
1-C
10Alkyl;
R
2Be sour destabilization protecting group; And
R
3And R
4Be hydrogen or methyl separately;
The relative quantity of a in the formula: b: c: d in weight portion, is 5～30: 100: 5～30: 5～70.
11. according to the polymkeric substance of claim 10, wherein this polymer repeating unit is represented by formula 3a:
[formula 3a]
The relative quantity of a in the formula: b: c: d in weight portion, is 5～30: 100: 5～30: 5～70.
12. a photo-corrosion-resisting agent composition, the light acid that comprises claim 1 produces polymkeric substance and organic solvent.
13., also comprise at least a light acid propellant, photoresist polymkeric substance and the components of additives of being selected from according to the photo-corrosion-resisting agent composition of claim 12.
14. according to the photo-corrosion-resisting agent composition of claim 13, wherein this photoresist polymkeric substance is a chemical amplifying type photoresist polymkeric substance.
15. according to the photo-corrosion-resisting agent composition of claim 14, wherein this photoresist polymkeric substance is represented by formula 4:
[formula 4]
The relative quantity of e in the formula: f: g in weight portion, is 100: 5～30: 40～70: 10～40.
16. according to the photo-corrosion-resisting agent composition of claim 13, wherein based on this photo-corrosion-resisting agent composition of 100 weight portions, polymkeric substance exists with the amount of 5～20 weight portions.
17. according to the photo-corrosion-resisting agent composition of claim 12, wherein this organic solvent is selected from: 3-methoxypropionic acid methyl esters, 3-ethoxyl ethyl propionate, propylene glycol methyl ether acetate, cyclohexanone, 2-heptanone, ethyl lactate and composition thereof.
18. according to the photo-corrosion-resisting agent composition of claim 12, wherein based on this photoresist polymkeric substance of 100 weight portions, organic solvent exists with the amount of 500～3000 weight portions.
19. a method of making semiconductor devices may further comprise the steps:
(a) photo-corrosion-resisting agent composition with claim 12 is coated on down on the coating, to form light actuating resisting corrosion film;
(b) this light actuating resisting corrosion film that exposes;
(c) light actuating resisting corrosion film that develops and exposed is to obtain the photoresist pattern; And
(d) this photoresist pattern is carried out etching process as etching mask,, thereby obtain coating pattern down with this time of etching coating.
20., comprise that the exposure sources that is used for immersion lithographic carries out this step of exposure (b) according to the method for claim 19.
21. according to the method for claim 19, also be included in this step of exposure (b) before the soft baking process or this step of exposure (b) afterwards after cure process.
22., be included under 70～200 ℃ the temperature and carry out this baking step according to the method for claim 21.
23. according to the method for claim 19, wherein the light source of this step (b) is selected from: F
2(157nm), ArF (193nm), KrF (248nm), E-bundle, EUV (far ultraviolet) and ion beam.
24., comprise with about 1～100mJ/cm according to the method for claim 19
2Exposure energy carry out this step of exposure (b).
25., comprise with alkaline development solution and carry out this development step (c) according to the method for claim 19.
26. semiconductor devices by the method preparation of claim 19.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR47324/05 | 2005-06-02 | ||
| KR1020050047323A KR100732300B1 (en) | 2005-06-02 | 2005-06-02 | Photoresist polymer for immersion lithography and photoresist composition comprising the same |
| KR47323/05 | 2005-06-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1873532A true CN1873532A (en) | 2006-12-06 |
| CN100590526C CN100590526C (en) | 2010-02-17 |
Family
ID=37484036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200510136300A Expired - Fee Related CN100590526C (en) | 2005-06-02 | 2005-12-27 | Polymer for immersion lithography, photoresist composition containing the same, method of manufacturing a semiconductor device, and semiconductor device |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR100732300B1 (en) |
| CN (1) | CN100590526C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102540703A (en) * | 2010-11-15 | 2012-07-04 | 罗门哈斯电子材料有限公司 | Compositions comprising base-reactive component and processes for photolithography |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3955419B2 (en) * | 1999-10-20 | 2007-08-08 | 富士フイルム株式会社 | Positive photoresist composition for deep ultraviolet exposure |
| KR20020009665A (en) * | 2000-07-26 | 2002-02-02 | 밍 루 | Guide rod combination structure of disk brake |
| KR100557555B1 (en) * | 2001-06-21 | 2006-03-03 | 주식회사 하이닉스반도체 | Photoresist Monomer Containing Fluorine-Substituted Benzylcarboxylate Group and Photoresist Polymer Comprising the same |
| KR100493015B1 (en) * | 2001-08-25 | 2005-06-07 | 삼성전자주식회사 | Photosensitive Polymer and Photoresist Composition Containing the Same |
-
2005
- 2005-06-02 KR KR1020050047323A patent/KR100732300B1/en not_active IP Right Cessation
- 2005-12-27 CN CN200510136300A patent/CN100590526C/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102540703A (en) * | 2010-11-15 | 2012-07-04 | 罗门哈斯电子材料有限公司 | Compositions comprising base-reactive component and processes for photolithography |
| CN102540703B (en) * | 2010-11-15 | 2014-10-01 | 罗门哈斯电子材料有限公司 | Compositions comprising base-reactive component and processes for photolithography |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100590526C (en) | 2010-02-17 |
| KR100732300B1 (en) | 2007-06-25 |
| KR20060125328A (en) | 2006-12-06 |
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