WO2004031858A2 - Resist system, use of a resist system and lithography method for the production of semiconductor elements - Google Patents

Resist system, use of a resist system and lithography method for the production of semiconductor elements Download PDF

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WO2004031858A2
WO2004031858A2 PCT/DE2003/003178 DE0303178W WO2004031858A2 WO 2004031858 A2 WO2004031858 A2 WO 2004031858A2 DE 0303178 W DE0303178 W DE 0303178W WO 2004031858 A2 WO2004031858 A2 WO 2004031858A2
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Prior art keywords
resist system
characterized
system according
resist
nm
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PCT/DE2003/003178
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German (de)
French (fr)
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WO2004031858A3 (en )
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Wolf-Dieter Domke
Oliver Kirch
Karl Kragler
Klaus Lowack
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Infineon Technologies Ag
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20Exposure; Apparatus therefor
    • G03F7/2002Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
    • G03F7/2004Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/0045Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/039Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition

Abstract

The invention relates to a resist system for lithography methods for the production of semiconductor components at wavelengths of 0.1 -150 nm, characterised by at least one polymer or copolymer comprising at least one acid-labile group. The invention also relates to the use of a resist system and a lithography method, whereby it is possible to obtain high sensitivity, especially in the EUV range, and no limitation of the process window occurs by undesirable cross-linking in the resist system, even at high doses of exposure.

Description

description

Resist system using a resist lithography system and method for the production of semiconductor devices

The invention relates to a resist system according to the preamble of claim 1, a use of a resist system of claim 13 and a lithography method according to the preamble of claim 14.

In microelectronics, so-called chemically amplified resist are (chemical amplification resists, CAR) for various optical lithography method (wavelengths: 248 nm, 193 nm, 157 nm) is used in a large scale. This is for example in the article by Hiroshi Ito "Deep-UV resists:

Evolution and Status ".. Describes Solid State Technology, July 1996, pp 164 et seq chemically amplified resists, especially with onium compounds as photo acid generators are also in Reichmanis et al.," Chemically amplified resists: Chemistry and Processes "

Advanced Materials for Optics and Electronics, Vol. 4, 83-93, discussed the 1994th

The resists may operate on the principle of acid-catalyzed cleavage. In the case of a positive resist this case is from a non-polar chemical group, such as a carboxylic acid tert-butyl ester group, in the presence of an acid generated by photolysis (Photo Acid Generator: PAG; photo-acid generator) formed a polar carboxylic acid group.

Course subordinates bases can influence the diffusion length of photo generated acid, which affects both

has Linienrauhigkeit and sensitivity of the resist system. In a subsequent development step, the exposed resist film is treated with an aqueous-alkaline developer solutions, the carboxylic acid-rich, polar regions are developed away, and stop the unexposed resist areas.

For the production of DRAMs by 2007 probably resist materials will be needed, the structures up to a size of 65 nm dissolve. For 2016 even the resolution of 22 nm DRAM half pitch will be necessary. With the currently used exposure wavelengths of 248 and 193 nm or even in the future used wavelength of 157 nm, these structures can no longer produce. Therefore, for future generations of lithography, optical lithography is in the extremely short wavelength of about 13 nm (EUV), or even in advance the X-ray range.

the requirements of the used resist material, both in terms of sensitivity and Linienrauhigkeit With decreasing feature size increase.

Furthermore, the effect is to be feared that the positively developable in the first step the photoresist becomes insoluble due to an excessive radiation dose again, resulting in a severe limitation of the process window result from the wavelength of 157 nm.

The present invention has for its object to provide a resist system and a lithography method with which a high sensitivity is provided in particular in the EUV range, at the same time but occurs no limitation of the process window due to undesired cross-linking in the resist system, even at high exposure doses.

This object is inventively achieved by a resist system having the features of claim 1. By at least one polymer or copolymer having at least one acid-labile group, a structuring at wavelengths in the range of 0.1 to 150 nm can surprisingly be made. The acid labile groups are cleaved under the catalytic Einwirkung_von acid and release polar groups, in turn, cause an increase in the solubility of the polymer / copolymer in developers, such as aqueous alkaline developers.

if at least one acid-labile group is a Estergruppe or a lactone group is advantageous.

Through the use of a copolymer of maleic anhydride with at least one segment and at least one methacrylate segment, a substrate may be patterned in a lithography process with wavelengths in the range of 0.1 to 150 nm, even without chemical strengthening agent. The resist system of the invention has a large process window, as no cross-links occur even at high exposure doses that lead to insolubility of the resist. Even if one always aims to use small exposure doses, so resist the inventive system is less sensitive by the large process window to variations in exposure.

It is particularly advantageous when a t-butyl methacrylate and / or a 2-ethoxyethyl methacrylate is used as the methacrylate segment.

The sensitivity of the resist system can be improved, when an iodine-containing and / or sulfur-containing photoacid generator is used as a chemical reinforcing agent.

In an advantageous embodiment, the resist system 10 of the invention has at least a photoacid generator is a Perfluoralkansulfuonat anion of the form C n F 2n + ι-χH x S0 3 ~ with n = l, ..., on.

Advantageously, at least a photoacid generator to an iodonium compound. It is particularly advantageous if at least one photoacid generator (tert. - butylphenyl) iodonium triflate is a di, di (tert -. Butylphenyl) iodoniumhexaflat, di (tert -. Butylphenyl) iodoniumnonaflat having diphenyliodonium, Diphenyliodoniumhexaflat or Diphenyliodoniumnonaflat.

It is also advantageous if at least one photoacid generator has a sulfonium compound, particularly a triphenylsulfonium triflate, triphenylsulfonium or Triphenylsulfoniumhexaflat.

Advantageously, resist system according to the invention on a proportion of silicon, which results in improved etch stability. It is particularly advantageous if the silicon in the form of a compound having a polymerizable carbon-carbon bond, in particular a Trimethylalylsilan is insertable into the resist system.

The object is also achieved by a use of the resist system and a method in which a resist system is used according to any one of claims 1 to 12th

The sensitivity when a resist system comprising a chemical amplification agent that contains at least one iodine and / or sulfur-containing photoacid generator is used in the inventive method is increased.

The large process window shown by the fact that the exposure dose in the inventive lithography process between 0.1 and 300 mJ / cm 2 may be. Even a massive over-exposure (eg by a factor of 250) does not lead to crosslinking of the polymer in the resist system. It is particularly advantageous when the exposure dose is in the exposure between 0.5 and 10 mJ / cm 2. The inventive method can be carried out at the wavelength of 0.1 to 150 nm. This covers the EUV range from up in the X-ray range. It is particularly advantageous to use a wavelength of 13.4 nm.

The invention is explained in detail below with reference to several embodiments.

According to the invention is a polymer component of

Resist system whose polarity is selectively changeable. In the following we describe the preparation of a polymer that is then usable alone or in conjunction with photo-acid generators as the inventive resist system.

The polymer is synthesized by radical polymerization. For this purpose,

20.27 g (206 mmol) maleic anhydride, 26.46 g (186 mmol) of t-butyl methacrylate,

3.27 g (21 mmol) of 2-ethoxyethyl methacrylate,

0.64 g (4 mmol) of α, α azoisobutyronitrile as free-radical initiator and 0.32 g (2 mmol) of dodecyl mercaptan as a chain regulator in 41.0 g (52 ml) of 2-butanone and 3 hours under reflux (80 to boiling heated ° C). Then, 4.0 g (5 ml) of methanol is added (for the partial alcoholysis of anhydride) and heating the reaction solution for a further 24 hours under reflux to boiling (80 ° C).

The mixture is allowed to cool to room temperature, the reaction solution and added with vigorous stirring 35.0 g (27,5ml) 2-propanol. The solution obtained is within 30 minutes with very vigorous mechanical stirring to a solution of 10.5 g (13.1 ml) of 2-butanone, 337.0 g (429 ml) of 2-propanol and 329.0 g (329 0 ml) of water added dropwise. Here, the polymer precipitates as a fine white powder. It is allowed for 30 minutes stirring and then the solvent is filtered off under slightly reduced pressure over a G3 frit.

The white precipitate (100 mL) washed with a solution of 16.0 g (20.0 ml) of 2-butanone, 111.0 g (141 ml) of 2-propanol and 100.0 g of water and 72 hours at 80 ° C dried under high vacuum. about 38 g is obtained (75% d. Th.) fine white powder as a reaction product. The analysis can be effected by means of NMR, GPC and DSC.

As an example of a silicon-containing polymer of the present invention Resistsysstems below a section is shown of a structure:

Figure imgf000007_0001

Alternatively, a silicon-free polymer can be used:

Figure imgf000007_0002
Example 1 (resist system with polymer without PAG)

5 g of the polymer described above is dissolved in 209 g 1-methoxy-2-propyl acetate. The solution is then pressure filtered through a Teflon filter with 0.2 micron pore. After 24 h rest period, a first embodiment of the resist system is ready for use. This first embodiment does not PAG.

The resist system is spin-coated on a silicon wafer (wafer) at 1000-5000 U / min and 90 s baked at 130 ° C (PAB). The layer thickness of the resist system is by spin coating at 3000 rev / min 110 nm. The exposure is performed with EUV light of wavelength 13.4 nm. The exposure dose D 0 is 36.8 mJ / cm 2. After exposure, a further baking step is carried out for 90 s at 130 ° C (PEB). The development is carried out in a 2.38% tetramethylammonium hydroxide solution, then the wafer is rinsed with distilled water and dried.

The effectiveness of this resist system, even without

Photoacid generators, is apparent from Fig. 1,.

Fig. 1 shows three points contrast curves in which the film thickness is plotted in nm on the exposure dose in mJ / cm 2. The right-hand curve ( "without PAG") shows the

Measured values of Example 1. Even without photoacid generator is up to exposure doses without possible to 10 mJ / cm 2 exposure. Thus, the sensitivity is in a range that is well used in practice.

Example 2 (resist system with di (tert. -

Butylphenyl) iodoniumhexaflat as PAG)

Basically have iodonium compounds on a structure (IR 2) X, wherein R may be an organic radical, in particular an aryl group. X is a hydroxy group or a monovalent acid radical. Possible structures include:

Figure imgf000009_0001

Wherein also the substituents R may be disposed on such a structure:

Figure imgf000009_0002

Suitable substituents R in particular linear or branched alkyl groups may be used, such as CH 3, C 2 H 5, isopropyl, or

CH,

-C-CH 3

CH3

The substituents R may be the same or identical to each other. As the anion of the photoacid generator may, for example, a Perfluoralkansulfuonat the form of S0 3 are each C n F 2n + ι-χH x "with n = l, ..., 10th

In the first embodiment 1 50 mg di (tert. Butylphenyl) to the polymer according to Example iodoniumhexaflat [(tBu-Ph) 2 J +, CF 3 CHF CF2SO3 "] propyl acetate as an iodonium compound in 209 g l-methoxy-2- dissolved. the solution is then pressure filtered through a Teflon filter with 0.2 micron pore. After 24 h rest period, a first embodiment of the resist system is ready for use.

The resist system is spin-coated on a silicon wafer (wafer) at 1000-5000 U / min and 90 s baked at 130 ° C (PAB). The layer thickness of the resist system is by spin coating at 3000 rev / min 110 nm. The exposure is performed with EUV light of wavelength 13.4 nm. The exposure dose D 0 is 1.4 mj / cm 2. After exposure, a further baking step, 90 seconds at 130 ° C (PEB). The development takes place in a 2:38% aqueous

Tetramethylammonium hydroxide, and then the wafer is rinsed with distilled water and dried.

Thus, a second embodiment of the resist system according to the invention is made.

Example 3 (resist system with triphenylsulfonium as photoacid generator)

Also the photoacid generator may comprise sulfonium compounds, in principle, [3 S R] + X have the shape of ~. A possible structure is for example a triphenylsulfonium (TPS):

Figure imgf000010_0001
The aromatic constituents may also have substituents R, which were listed in the above example.

The preparation of a third embodiment of the resist system according to the invention is carried out analogously to Example 2, however, [CF 3 (CF 2) 3 S0 3 ~ Ph 3 S +,] is used instead of di (tert-butylphenyl) iodoniumhexaflat as photoacid generator Triphenylsulfoniumnnonaflat used. The exposure dose is in this embodiment 2.4 mJ / cm 2.

Example 4 (resist system with triphenylsulfonium nonaflate and base) The preparation of a fourth embodiment of the resist system according to the invention is carried out analogously to Example 3, but additionally be 3 mg

Triphenylsulfonium added as a base to the solution. The exposure dose was 4.1 mJ / cm 2. The contrast behavior of this embodiment is the middle curve in Fig. 1 ( "PAG Base +"). The sensitivity is also maintained by the addition of small amounts of base, even if the sensitivity is lower than in the left curve in FIG. 1, that when using a polymer of the invention with PAG without a base.

Example 5 (resist system with diphenyliodonium)

In a fifth embodiment, a resist system is analogous to Example 2, wherein (tert. - butylphenyl) instead of the Di iodoniumhexaflat as photoacid generator

Diphenyliodonium [Ph 2 I, CF 3 S0 3 ~ +] is used. The exposure dose is 1.3 mJ / cm 2.

Example 6 (resist system with triphenylsulfonium) In a sixth embodiment, for example, 2 prepared in analogy to a resist system, (tert. Butylphenyl) instead of the Di iodoniumhexaflat as photoacid generator triphenylsulfonium [Ph 3 S + CF 3 S0 3 ~] is used. The exposure dose was 0.8 mJ / cm 2.

The left curve in FIG. 1 is a contrast curve, which were ermitttelt with a resist system according to this embodiment. This makes it clear that the PAG significantly improves the sensitivity so that even at low exposure doses good results are achieved.

But it can also be used a much higher exposure dose of 250 mJ / cm 2. The resist system works even with these high doses without causing undesirable cross-links.

Example 7 (resist system with Triphenylsulfoniumhexaflat)

In a seventh embodiment, a resist system is analogous to Example 2, wherein (tert. - butylphenyl) instead of the Di iodoniumhexaflat as photoacid generator Triphenylsulfoniumhexaflat [Ph 3 S + CF 3 CF 2 CHF S0 3 ~] is used. The exposure dose is 1.6 mJ / cm 2.

The example 2 to 7 show some specified combinations of the photoacid generators. In principle, possible permutations of triphenylsulfonium, diphenyliodonium, and di (tert. Butylphenyl) iodonium salts of trifluorosulfonic acid (triflates), the Hexafluorsulfonsäure (Hexaflate) or Nonafluorsulfonsäure (nonaflates) suitable.

The invention is not limited in its implementation to the above preferred embodiments. Rather, a number of variants which make use of the resist system according to the invention and the lithographic process according to the invention even with fundamentally different embodiments use.

Claims

claims
1. resist system for lithographic process for the production of semiconductor devices at wavelengths in the range of 0.1 to 150 nm, characterized by at least one polymer or copolymer having at least one acid-labile group.
2. resist system of claim 1, characterized in that at least one acid labile group is a Estergruppe or a lactone group.
3. Resist system according to claim 1 or 2, characterized by a copolymer having at least one
Maleic anhydride segment and at least one methacrylate segment.
4. Resist system according to claim 3, characterized in that the methacrylate segment is a t-butyl methacrylate and / or 2-ethoxyethyl.
5. Resist system according to at least one of the preceding claims, characterized by at least one iodine and / or sulfur-containing photo-acid generator as a chemical reinforcing agent.
6. Resist system according to claim 5, characterized in that at least a photoacid generator is a Perfluoralkansulfuonat 3 ", ..., having anion of the form C n F 2n + ι-χH x S0 with n = l 10th
7. Resist system according to claim 5 or 6, characterized in that at least one photo-acid generator having an iodonium compound.
8. iodonium triflate resist system according to at least one of claims 5 to 7, characterized in that at least a photoacid generator is a di, di (tert butylphenyl.) Iodoniumhexaflat, di (tert (tert butylphenyl.). -
Butylphenyl) iodoniumnonaflat having diphenyliodonium, Diphenyliodoniumhexaflat or Diphenyliodoniumnonaflat.
9. Resist system according to at least one of the preceding
Claims, characterized in that at least one photoacid generator has a sulfonium compound.
10. Resist system according to claim 9, characterized in that at least a photoacid generator is a
comprising triphenylsulfonium triflate, triphenylsulfonium or Triphenylsulfoniumhexaflat.
11. Resist system according to at least one of the preceding claims, characterized by a proportion of silicon.
12. Resist system according to claim 11, characterized in that the silicon in the form of a compound having a polymerizable carbon-carbon bond, in particular a trimethylallylsilane is insertable into the resist system.
13. The use of a resist system according to at least one of claims 1 to 12 in a lithography process for producing semiconductor components in a wavelength range of 0.1 to 150 nm, especially 13.4 nm.
14. lithography process for producing
Semiconductor devices, a resist system according to one of claims 1 to 12, characterized by a) applying the resist system to a substrate, in particular a wafer,
b) exposing the resist system on the substrate,
c) Development of the resist system.
15. lithography method according to claim 14, characterized in that the polymer prior to the application of the resist system with a chemical reinforcing agent, which is mixed at least one iodine and / or sulfur-containing photoacid generator.
16. lithography method according to claim 14 or 15, characterized in that the exposure dose in the exposure between 0.1 and 300 mJ / cm 2.
17. lithography process according to any one of claims 14 to 16, characterized in that the exposure dose in the exposure between 0.5 and 10 mJ / cm 2.
18. The method according to at least one of claims 14 to 17, characterized in that the wavelength in the exposure 0.1 to 150 nm, especially 13.4 nm.
PCT/DE2003/003178 2002-09-30 2003-09-19 Resist system, use of a resist system and lithography method for the production of semiconductor elements WO2004031858A3 (en)

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